Catalyzed Hydroamination Reactions Lutz Ackermann Georg-August-Universität Göttingen
|
|
- Cory Garrison
- 6 years ago
- Views:
Transcription
1 Catalyzed ydroamination eactions Lutz Ackermann Georg-August-Universität Göttingen
2 Overview Introduction ydroamination of Alkynes 1 Activation of the Amine 2 Activation of the Alkyne ydroamination of Alkenes 1 Activation of the Amine 2 Activation of the Alkene
3 1 Literature eview Articles: General reviews: - Brunet, J. J.; eibecker, D. In Catalytic eterofunctionalization; Togni, A., Grützmacher,., Eds.; Wiley-VC: Weinheim, 2001; pp Beller, M.; Seayad, J.; Tillack, A.; Jiao,. Angew. Chem., Int. Ed. 2004, 43, Müller, T. E.; ultzsch, K. C.; Yus, M; Foubelo, F.; Tada, M. Chem. ev. 2008, 108,
4 1 Why ydroamination? Amines, imines and enamines are - important bulk and fine chemicals - biologically active compounds - versatile synthetic intermediates O O latonin (tissue hormone) O Verapamil (cardiac drug) O CO 2 Tromaril (anti-inflammatory)
5 1 Atom-Efficient Alternative
6 1 ydroamination of Alkenes, Alkynes, and Allenes
7 1 egioselectivity
8 1 Obstacles - Addition of 3 or simple amines to unactivated alkenes is feasible slightly exothermic or approximately thermoneutral, e.g C C 2 Δ = kj/mol, ΔS = J/mol, ΔG = kj/mol Steinborn, D.; Taube,. Z. Chem. 1986, 26, Attack of the amine nitrogen on electron-rich (non-activated) multiple bonds leads to electrostatic repulsion. high activation barrier - Concerted [2+2] addition of the bond to the alkene is orbital-symmetry forbidden - Intermolecular hydroamination reactions: negative reaction entropy ΔS
9 1 Uncatalyzed Addition eactions: Conjugate Addition Uncatalyzed direct nucleophilic addition of amines proceeds easily only with electron-deficient (activated) C C multiple bonds (aza-michael addition, conjugate addition). EWG EWG EWG EWG EWG = C(O), CO 2, C, S(O), O 2,... for the hydroamination of electronically unactivated C C multiple bonds, catalysts are mandatory!
10 1 chanistic Considerations Activation of the Amine ydroamination of alkynes
11 1 chanistic Considerations Activation of the Amine ydroamination of alkenes
12 1 chanistic Considerations Activation of the C-C Multiple Bond Activation of alkynes
13 2 ydroamination eactions of Alkynes 2.1 Activation of the Amine
14 2.1 Alkali tals - Efficient Catalyst + KO (18 mol %) decaline, C eppe, W.; Keyssner, E. (I. G. Farbenindustrie AG) DE618120, 1935.
15 2.1 Lanthanide-Based Catalysts Ph + 2 Pr 2 Si(C 5 4 ) 2 dc(tms) 2 (1.3 mol %) C 6 D 6, 60 C Ph Pr 85 % Li, Y.; Marks, T. J. Organometallics 1996, 15, activation of the amine regioselective intra- and intermolecular hydroamination reactions primary and secondary amines relatively mild reaction conditions rigorously anhydrous/anaerobic reaction conditions
16 2.1 Lanthanide Complexes as Catalysts Amido-chanism 1 [Ln] [Ln] [Ln] 2 1 [Ln] 1 2
17 2.1 Titanium Catalysts Intermolecular eactions SiO 2 O Cp 2 Ti 2 (3.0 mol %) Ph Ph + Ph 2 Ph, 100 C Ph Ph Ph 92 % LiAl 4 Ph Ph Ph 62 % Ph Ph Angew. Chem., Int. Ed. 1999, 38, restricted to primary amines
18 2.1 Catalyst Preparation Ph + Ph 2 [Ti] (3-10 mol %) Ph, C Ph Ph > 92 % Ti Cl Cl + 2 Li - 2 LiCl Ti 48 / 25 g TiCl Li 2-4 LiCl Ti( 2 ) 4 2 / 25 g 576 / 25 g side-product formation (LiCl) strong bases mediate hydroamination themselves
19 2.1 TiCl 4 as Precatalyst - Scope TiCl 4 (10-20 mol%), tbu Ph, 105 C strong external base is not required for catalyst preparation Organometallics 2003, 22,
20 2.1 Group IV-Transition tal Catalysts - chanism 1 1 Cp 2 M( 1 ) Cp 2 M 1 M = Zr, Ti (, U) imido complex catalytically competent formal [2+2] cycloaddition protonolysis rate-limiting step 1 1 [M] Cp 2 M Zr, Ti: Bergman,. G. et al. J. Am. Chem. Soc. 1992, 114, ; J. Am. Chem. Soc. 2001, 123, U: Eisen, M. S. et al. Organometallics 2001, 20,
21 2 ydroamination eactions of Alkynes 2.2 Activation of the Alkyne
22 2.2 rcury-based Catalyst n-pent + go (4-12 mol %) 2 Ph BF 3 OEt 2 (3-9 mol %) C n-pent Ph C 2 = % = Et 19 % Loritsch, J. A.; Vogt,.. J. Am. Chem. Soc. 1939, 61, n-pent + PhEt gcl 2 (5 mol %) TF, 60 C, 1 h n-pent Et C 3 Ph + n-pent Et C 2 Ph 84 % >95 < 5 Barluenga, J; Aznar, F.; Liz,.; odes,. J. Chem. Soc., Perkin Trans , primary and secondary amines high toxicity of catalysts
23 2.2 Thallium-Based Catalyst Ph + 2 Ph Tl(OAc) 3 (2 mol %) no solvent, 60 C, 7 h Ph C 3 Ph 57 % Ph + Ph Tl(OAc) 3 (2 mol %) no solvent, 60 C, 7 h Ph C 2 Ph 31 % Barluenga, J; Aznar, F. Synthesis 1977, 195. primary and secondary amines high toxicity of catalysts
24 2.2 Gold-Based Catalyst Intermolecular ydroamination 2 aaucl O (5 mol %) C, reflux, 1h ex 80 % ex Fukuda, Y.; Utimoto, K.; ozaki,. eterocycles 1987, 25, (PPh 3 )Au (0.1 mol %) Ph + Br 3 PW 12 O 40 (0.5 mol %) no solvent, 70 C, 2 h Ph C 3 94 % Br Mizushima, E.; ayashi, T.; Tanaka, M. Org. Lett. 2003, 5, highly efficient terminal and internal alkynes primary aniline derivatives, no alkyl amines Markovnikov selectivity
25 2.2 Au-Catalyzed ydroamination Proposed chanism [Au] 2 Ar Ar coordination [Au] 1 1 Ar 2 inner-sphere C- bond formation [Au] 2 Ar 2 Mizushima, E.; ayashi, T.; Tanaka, M. Org. Lett. 2003, 5, eview: Widenhoefer,. A.; an, X. Eur. J. Org. Chem. 2006,
26 2.2 Platinum Catalyst Bu + 2 Ph PtBr 2 (0.3 mol %) no solvent, 60 C, 4 d Bu C 3 Ph 28 % Ph + 2 Ph PtBr 2 (0.3 mol %), + (0.9 mol %) no solvent, 100 C, 2 d Ph C 3 Ph 44 % relatively low catalytic activity side-products due to transfer hydrogenation (e.g. amines and quinolines) are formed terminal alkynes and primary anilines Markovnikov selectivity Brunet, J.-J. et al. J. Mol. Catal. A: Chem. 2005, 240,
27 2.2 Palladium-Based Catalyst Early Intramolecular ydroaminations O Et 2 ex Et PdCl 2 (1 mol %) 84 % C, reflux, 3h ex Utimoto, K.; Miwa,.; ozaki,. Tetrahedron Lett. 1981, 22, Bu 2 PdCl 2 (5.0 mol %) C, reflux, 1h Bu 81 % Utimoto, K.; et al. Tetrahedron Lett. 1988, 29,
28 2 ydroamination of Alkynes - Summary 3 catalyst Alkynes are usually less easily accessible when compared to alkenes Through activation of amines: - Alkali tals, Ln, An, early TM (Ti, Zr) - Oxidative addition with late TM (u) - anti-markovnikov selectivity can be achieved Through activation of alkynes: - Traditionally with g, Tl (highly toxic) - Late transition metals (Au, Pd, h, Pt, ) - Usually provide Markovnikov selectivity with good functional group tolerance
29 3 ydroamination eactions of Alkenes 3.1 Activation of the Amine
30 3.1 Base-Catalysis Early Examples - base-catalyzed hydroamination reactions + M' + 2 M 2 M - ' M 2 e.g. Li, Li 2, a 2, KOt-Bu, a eview: Adv. Synth. Catal. 2002, 344, an early example: a (4 mol %) + pyridine, 100 C 28 bar 83 % owk, B. W.; Little, E. L.; Scott, S. L.; Whitman, G. M. J. Am. Chem. Soc. 1954, 76, Wollensak, J.; Closson,. D. Org. Synth. 1973, 5, => intermolecular hydroamination of unactivated olefins under relatively harsh conditions
31 3.1 Base-Catalyzed ydroamination Industrial Applications LiEt 2 (1 mol %) Et 2, 92 % Et 2 O myrcene diethylgeranylamine Takasago ( )-menthol process
32 3.1 Synthesis of Biologically Active Compounds - application to the synthesis biologically active compounds - anti-markovnikov addition to styrenes + Bn n-buli (10 mol %), TF, 65 C Bn = Cl: 38 % = : 75 % O Ar Serotonin (5-T)-receptor (schizophrenia, Parkinson s desease, depression, ) Chem. Eur. J. 2004, 10,
33 3.1 Base-Catalyzed ydroamination - chanism - mechanism 2 M'' important features: 2 M '' inexpensive catalysts, but tolerate only few functional groups 2 ' ' fast slow 2 2 M '
34 3.1 Organolanthanide as Catalyst 2 n Cp* 2 LaC(TMS) 2 (3 mol %) Ph, 60 C n n = 1: TOF = 140 h -1 n=2:tof=5h -1 Gagné, M..; Marks, T. J. J. Am. Chem. Soc. 1989, 111, Pr 2 2 Si(C 5 4 ) 2 dc(tms) 2 (20 mol %) C 6 D 6, 60 C Pr 90 %, TOF = 0.4 h -1 Li, Y.; Marks, T. J. Organometallics 1996, 15, significantly lower reactivity in intermolecular hydroaminations - Markovnikov selectivity
35 3.1 Organolanthanides as Catalysts - chanism L 2 Ln 2 L 2 Ln 2 L 2 Ln Gagné, M..; Marks, T. J. J. Am. Chem. Soc. 1989, 111, eview: ong, S.; Marks, T. J. Acc. Chem. es. 2004, 37,
36 3.1 Ti( 2 ) 4 -Catalyzed Intramolecular ydroamination Ph Ph Ti( 2 ) 4 (5 mol %) 2 Ph, 110 C, 24 h Ph Ph 92 % Org. Lett. 2005, 7, Intermolecular eactions: Angew. Chem. Int. Ed. 2005, 44, Enantioselective: Angew. Chem. Int. Ed. 2007, 46, primary amines - secondary amines are not converted - imido mechanism
37 3.1 Ti( 2 ) 4 -Catalyzed ydroamination - chanism L 2 Ti( 2 ) L 2 Ti imido complex catalytically competent formal [2+2] cycloaddition protonolysis rate-limiting step 1 L 2 Ti L 2 Ti 2 1
38 3.1 Iridium-Catalyzed ydroaminations + Ph 2 (PEt 3 ) 2 Ir(C 2 4 ) 2 Cl (10 mol %) ZnCl 2 (2 mol %), TF, reflux Ph TOF = 0.08 h -1 Milstein, D. et al. J. Am. Chem. Soc. 1988, 110, artwig, J. F. et al. Science 2005, 307, Ph 2 [(PP*)IrCl] (1-2 mol %) "F - ", 75 C (2S) Ph (2) Ph - first intermolecular asymmteric hydroamination PP* = (,S)-Josiphos, yield: 81 % 31 % 69 % PP* = (S)-BIAP, yield: 22 % 2.5 % 97.5 % Togni, A. et al. J. Am. Chem. Soc. 1997, 119,
39 3.1 Iridium-Catalyzed ydroamination - chanism Ph 2 Ph (PEt 3 ) 2 IrCl oxidative addition of aniline 2 P 2 P Ph Ir Cl x-ray (PEt 3 ) 2 Ir(Ph)()Cl J. Am. Chem. Soc. 1988, 110,
40 3 ydroamination eactions of Alkenes 3.2 Activation of the Alkene
41 3.1 Palladium-Catalyzed Intermolecular ydroamination + [Pd(PPh 3 ) 4 ] (2 mol %) Ph 2 Ph TFA (20 mol %) Ph, 100 C, 12 h 83 % artwig, J. F. et al. J. Am. Chem. Soc. 2000, 122, See also: Ozawa, F. et al. Angew. Chem. Int. Ed. 2001, 40, O [Pd(O 2 CCF 3 ) 2 ] (5 mol %) dppf (10 mol %) TFA (20 mol %) dioxane, 120 C, 24 h artwig, J. F. et al. J. Am. Chem. Soc. 2003, 125, intermolecular hydroamination (also with an alkyl)amine with Markovnikov selectivity - limited to vinylarenes - primary and secondary amines - Brønsted acid as cocatalyst - enantioselective hydroamination reported (up to 63 % ee) O 75 %
42 3.1 Palladium-Catalyzed ydroamination Ph, OTf Ph Ar, OTf L 2 Pd - illustrated for Pd (O) Ph Ph Ar L 2 Pd Ph 2 Ar OTf PdL 2 Ar 2 artwig, J. F. et al. J. Am. Chem. Soc. 2006, 128,
43 3.1 Pd-Catalyzed ydroamination: Initiation for Pd(II) 2 PdL L 2 Pd(OTf) 2 CF 3 Ph, 80 C % 2+ PdL Ar Ar + L PdL 2 Pd Ar - Ph artwig, J. F. et al. J. Am. Chem. Soc. 2002, 124, palladium hydride is relevant - η 3 -benzyl complex characterized by x-ray diffraction
44 3.2 Platinum-Catalyzed Intermolecular ydroamination 2 C PtBr2, Bu4PBr, TFA 150 C, 96 h + C 4 9 TO > % 5% Brunet, J.-J. et al. Organometallics 2004, 23, ; Organometallics 2005, 24, ; Organometallics 2006, 25, highly active - applicable simple alkyl-substituted alkenes - not air-sensitive - Markovnikov selectivity
45 3.2 Platinum-Catalyzed Intramolecular ydroamination Ph Ph Bn [PtCl 2 ( 2 C=C 2 )] 2 (2.5 mol %) PPh 3 (5.0 mol %) 1,4-dioxane, 120 C, 16 h Ph Ph Bn 75 % Wiedenhoefer,. A. et al. J. Am. Chem. Soc. 2005, 127, For less basic (sulfon)amides, see: Wiedenhoefer,. A. et al. Org. Lett. 2005, 7, ; Tilley, T. D. et al. J. Am. Chem. Soc. 2005, 127, basic secondary alkylamines can be cyclized - Less basic -nucleophiles (e.g. amides) can be added to alkenes with Au-based catalysts: e.g. e, C. et al. J. Am. Chem. Soc. 2006, 128, ; Angew. Chem., Int. Ed. 2006, 45, Wiedenhoefer,. A. et al. Org. Lett. 2006, 8, ; Angew. Chem., Int. Ed. 2006, 45, ; Chem. Commun. 2006, ; eview: Widenhoefer,. A.; an, X. Eur. J. Org. Chem. 2006,
46 3.2 Platinum-Catalyzed Intramolecular ydroamination - chanism [Pt] Bn Bn, Bn Bn [Pt] [Pt] Wiedenhoefer,. A. et al. J. Am. Chem. Soc. 2005, 127,
47 3 Alkene ydroamination Summary & Conclusion Activation of amines - Alkali metal-based catalysts: industrial processes, limited functional group tolerance - Ln-based catalysts: efficient intramolecular reactions, very sensitive - Group IV transition metal-based catalysts: intramolecular, asymmetric - Iridium-catalyzed (asymmetic) intermolecular hydroamination of strained alkenes Activation of alkenes: - Markovnikov hydroamination with Pd-, Pt- and (Au)-based catalysts (mainly intramolecular or conjugated alkenes, excetion ethylene) - anti-markovnikov hydroamination of conjugated alkenes with h- and u-based catalysts Generally applicable catalysts for intermolecular, particularly anti-markovnikov, hydroaminations of non-conjugated alkenes are highly desirable!
Direct Oxidative Heck Cyclizations: Intramolecular Fujiwara-Moritani Arylations for the Synthesis of Functionalized Benzofurans and Dihydrobenzofurans
Direct xidative eck Cyclizations: Intramolecular Fujiwara-Moritani Arylations for the Synthesis of Functionalized Benzofurans and Dihydrobenzofurans by Zhang,.; Ferreira, E. M.; Stoltz, B. M. Angewandte
More informationAdditions to Metal-Alkene and -Alkyne Complexes
Additions to tal-alkene and -Alkyne Complexes ecal that alkenes, alkynes and other π-systems can be excellent ligands for transition metals. As a consequence of this binding, the nature of the π-system
More informationDirect, Catalytic Hydroaminoalkylation of Unactivated Olefins with N-Alkyl Arylamines
Current Literature - May 12, 2007 Direct, Catalytic ydroaminoalkylation of Unactivated lefins with -Alkyl ylamines ' '' Ta[ 2 ] 5 (4-8 mol%), 160-165 o C 24-67h 66-95% ' '' S. B. erzon and J. F. artwig,
More informationStrained Molecules in Organic Synthesis
Strained Molecules in rganic Synthesis 0. Introduction ~ featuring on three-membered rings ~ Tatsuya itabaru (M) Lit. Seminar 08068 for cyclobutadienes : see Mr. Yamatsugu's Lit. Sem. 069 eat of Formation
More informationFunctionalization of C(sp 3 ) H Bonds Using a Transient Directing Group
Literature eport Functionalization of C(sp 3 ) Bonds Using a Transient Directing Group eporter: Mu-Wang Chen Checker: Yue Ji Date: 2016-04-05 Yu, J.-Q. et al. Science 2016, 351, 252-256. Scripps esearch
More informationElectrophilic Carbenes
Electrophilic Carbenes The reaction of so-called stabilized diazo compounds with late transition metals produces a metal carbene intermediate that is electrophilic. The most common catalysts are Cu(I)
More informationHighlights of Schmidt Reaction in the Last Ten Years
ighlights of Schmidt eaction in the Last Ten Years Dendrobates histrionicus Jack Liu ov. 18, 2003 Introduction Classical Schmidt reaction of aldehydes and carboxylic acids Classical Schmidt reaction of
More informationMetal Catalyzed Outer Sphere Alkylations of Unactivated Olefins and Alkynes
Metal Catalyzed uter Sphere Alkylations of Unactivated lefins and Alkynes Stephen Goble rganic Super-Group Meeting Literature Presentation ctober 6, 2004 1 utline I. Background Introduction to Carbometallation
More informationAnti-Markovnikov Olefin Functionalization
Anti-Markovnikov Olefin Functionalization ~Prof. Robert H. Grubbs Work~ 4 th Literature Seminar July 5, 2014 Soichi Ito (D1) Contents 1. Introduction Flow of Prof. Grubbs Research Markovnikov s Rule Wacker
More informationHomogeneous Catalysis - B. List
omogeneous Catalysis - B. List 2.2.2 Research Area "rganocatalytic Asymmetric α-alkylation of Aldehydes" (B. List) Involved:. Vignola, A. Majeed Seayad bjective: α-alkylations of carbonyl compounds are
More informationZr-Catalyzed Carbometallation
-Catalyzed Carbometallation C C C C ML n C C ML n ML n C C C C ML n ML n C C ML n Wipf Group esearch Topic Seminar Juan Arredondo November 13, 2004 Juan Arredondo @ Wipf Group 1 11/14/2004 Carbometallation
More informationChiral Catalyst II. Palladium Catalysed Allylic Displacement ( -allyl complexes) 1. L n Pd(0) 2. Nuc
Chiral Catalyst II ast lecture we looked at asymmetric catalysis for oxidation and reduction Many other organic transformations, this has led to much investigation Today we will look at some others...
More informationMolybdenum-Catalyzed Asymmetric Allylic Alkylation
Molybdenum-Catalyzed Asymmetric Allylic Alkylation X MoL n u u * Tommy Bui 9/14/04 Asymmetric Allylic Alkylation from a Synthetic Viewpoint X X M u u * and/or u form a C-C bond with the creation of a new
More informationhttps://cuvillier.de/de/shop/publications/766
Jelena Jenter (Autor) Nitrogen Donor Ligands in the Coordination Chemistry of the are Earth and Alkaline Earth Metals Synthesis - Structures - Catalysis https://cuvillier.de/de/shop/publications/766 Copyright:
More informationAsymmetric Catalysis by Lewis Acids and Amines
Asymmetric Catalysis by Lewis Acids and Amines Asymmetric Lewis acid catalysis - Chiral (bisooxazoline) copper (II) complexes - Monodentate Lewis acids: the formyl -bond Amine catalysed reactions Asymmetric
More informationCatellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo
Catellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo 2014.1.6 1 Content Introduction Progress of Catellani Reaction o-alkylation and Applications o-arylation and Applications Conclusion and Outlook
More informationR 2 R 4 Ln catalyst. This manuscript describes the methods for the synthesis and application of group 4 metallocene bis(trimethylsilyl)acetylene
VII Abstracts 2011 p1 2.12.15 rganometallic Complexes of Scandium, Yttrium, and the Lanthanides P. Dissanayake, D. J. Averill, and M. J. Allen This manuscript is an update to the existing Science of Synthesis
More informationC H Activated Trifluoromethylation
Literature report C H Activated Trifluoromethylation Reporter:Yan Fang Superior:Prof. Yong Huang Jun. 17 th 2013 Contents Background Trifluoromethylation of sp-hybridized C-H Bonds Trifluoromethylation
More informationLecture 6: Transition-Metal Catalysed C-C Bond Formation
Lecture 6: Transition-Metal Catalysed C-C Bond Formation (a) Asymmetric allylic substitution 1 u - d u (b) Asymmetric eck reaction 2 3 Ar- d (0) Ar 2 3 (c) Asymmetric olefin metathesis alladium π-allyl
More informationsp 3 C-H Alkylation with Olefins Yan Xu Dec. 3, 2014
sp 3 C-H Alkylation with Olefins, Yan Xu Dec. 3, 2014 1) sp 3 C-H Alkylation via Directed C-H activation 2) Hydroaminoalkylation (still via C-H activation) 3) Hydrohydroxyalkylation (via radical chemistry)
More informationCatalytic alkylation of remote C H bonds enabled by proton-coupled electron transfer
Catalytic alkylation of remote C bonds enabled by proton-coupled electron transfer Reporter: Ji Zhou Checker: Shubo u Date: 2016/11/14 Choi, G. J.; Zhu, Q.-L.; Miller, D. C.; Gu, C. J.; Knowles, R. R.
More information"-Amino Acids: Function and Synthesis
"-Amino Acids: Function and Synthesis # Conformations of "-Peptides # Biological Significance # Asymmetric Synthesis Sean Brown MacMillan Group eting ovember 14, 2001 Lead eferences: Cheng,. P.; Gellman,
More informationSpiro Monophosphite and Monophosphoramidite Ligand Kit
Spiro Monophosphite and Monophosphoramidite Ligand Kit metals inorganics organometallics catalysts ligands custom synthesis cgm facilities nanomaterials 15-5162 15-5150 15-5156 15-5163 15-5151 15-5157
More informationA Simple Introduction of the Mizoroki-Heck Reaction
A Simple Introduction of the Mizoroki-Heck Reaction Reporter: Supervisor: Zhe Niu Prof. Yang Prof. Chen Prof. Tang 2016/2/3 Content Introduction Intermolecular Mizoroki-Heck Reaction Intramolecular Mizoroki-Heck
More informationOxidative couplings of two nucleophiles
Oxidative Couplings of Hydrocarbons Oxidative couplings of two nucleophiles Oxidants involved: O 2 H 2 O 2 high h valent metals(copper salts) halides(iodine(Ⅲ) oxidants) Lei, A. W. Chem. Rev., 2011, 111,
More informationRecent Advancements In The [2+2+2] Cycloaddition. Brandon Dutcher January 17, 2007 Michigan State University
ecent Advancements In The [2+2+2] Cycloaddition Brandon Dutcher January 17, 2007 ichigan tate University utline verview of [2+2+2] cycloaddition chanism of the [2+2+2] cycloaddition Issues with selectivity
More informationChiral Brønsted Acid Catalysis
Chiral Brønsted Acid Catalysis Aryl Aryl Aryl Aryl S CF 3 2 P Fe CF 3 CF 3 2 Jack Liu ov. 16, 2004 CF 3 Introduction Chiral Brønsted acid catalysis in nature: enzymes and peptides Chiral Brønsted acid
More informationBifunctional Asymmetric Catalysts: Design and Applications. Junqi Li CHEM Sep 2010
Bifunctional Asymmetric Catalysts: Design and Applications Junqi Li CHEM 535 27 Sep 2010 Enzyme Catalysis vs Small-Molecule Catalysis Bronsted acid Lewis acid Lewis acid Bronsted base Activation of both
More informationTotal Syntheses of Minfiensine
Total Syntheses of Minfiensine Douany, A. B.; umphreys, P. G.; verman, L. E.*; Wrobelski, A. D., J. Am. Chem. Soc. 2008, ASAP. D: 10.1021/ja800163v Shen, L.; Zhang, M.; Wu, Y.; Qin, Y.*, Angew. Chem. nt.
More informationNucleophilic Fluorination. Souvik Rakshit Burke group Literature Seminar July 13, 2013
Nucleophilic Fluorination Souvik Rakshit Burke group Literature Seminar July 13, 2013 Relevance 20% of pharmaceuticals contain fluorine 5-fluorouracil Antineoplastic agent, 1957 Lipitor (Atorvastatin)
More informationNegishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides
Negishi Coupling of Secondary Alkylzinc alides with Aryl Bromides and Chlorides X X = Br, Cl 2 1 ZnBr 1, 2 = Alkyl Cat. Pd(OAc) 2 Ligand TF/Toluene rt or 60 o C 1 2 J. Am. Chem. Soc. 2009, ASAP Article
More informationVI. Metal alkyls from oxidative addition / insertion
V. Metal alkyls from oxidative addition / insertion A. Carbonylation - C insertion very facile, metal acyls easily cleaved, all substrates which undergo oxidative addition can in principle be carbonylated.
More informationChapter 4 Electrophilic Addition to Carbon Carbon Multiple Bonds 1. Addition of H X 2. Addition of H OH and addition of Y X 3. Addition to allene and
Chapter 4 Electrophilic Addition to Carbon Carbon Multiple Bonds 1. Addition of X 2. Addition of and addition of Y X 3. Addition to allene and alkyne 4. Substitution at α-carbon 5. eactions via organoborane
More informationEnantioselective Borylations. David Kornfilt Denmark Group Meeting Sept. 14 th 2010
Enantioselective Borylations David Kornfilt Denmark Group Meeting Sept. 14 th 2010 30.000-foot View Enantioenriched Organoboranes What to do with them Crudden C. M. et. al., Eur. J. Org. Chem. 2003, 46
More informationHydrogen-Mediated C-C Bond Formation
EPFL - ISIC - LSPN Hydrogen-Mediated C-C Bond Formation History and selected examples The Research of Prof. Michael Krische (University of Texas at Austin) LSPN Group Seminar Mathias Mamboury Table of
More informationDenmark Group Meeting. & Electrophilic rearrangement of amides
Denmark Group Meeting Palladium catalyzed Dearomatizationeaction & Electrophilic rearrangement of amides 11 th Bo Peng th Feb. 2014 1 https://maps.google.com 2 Palladium catalyzed Dearomatization eaction
More informationNickel-Catalyzed Three-Component [3+2+2] Cocyclization of Ethyl Cyclopropylideneacetate and Alkynes
Nickel-Catalyzed Three-Component [3+2+2] Cocyclization of Ethyl Cyclopropylideneacetate and Alkynes Selective Synthesis of Multisubstituted Cycloheptadienes 1 2 Cat. Ni 0 1 2 Komagawa, S.; Saito, S. Angew.
More informationPalladium-catalyzed alkylation of unactivated olefins*
Pure Appl. Chem., Vol. 76, No. 3, pp. 671 678, 2004. 2004 IUPAC Palladium-catalyzed alkylation of unactivated olefins* Ross A. Widenhoefer P. M. Gross Chemical Laboratory, Duke University, Durham, NC 27708-0346,
More informationAsymmetric Radical Reactions. Zhen Liu 08/30/2018
Asymmetric adical eactions Zhen Liu 08/30/2018 Contents Introduction eactions Using Chiral Auxiliary Chiral Lewis Acid-diated eactions Transition tal-catalyzed eactions eactions Using Chiral rganocatalysts
More informationLiterature Report III
Literature Report III Regioselective ydroarylation of Alkynes Reporter: Zheng Gu Checker: Cong Liu Date: 2017-08-28 Cruz, F. A.; Zhu, Y.; Tercenio, Q. D.; Shen, Z.; Dong, V. M. J. Am. Chem. Soc. 2017,
More informationSuggested solutions for Chapter 40
s for Chapter 40 40 PBLEM 1 Suggest mechanisms for these reactions, explaining the role of palladium in the first step. Ac Et Et BS () 4 2 1. 2. K 2 C 3 evision of enol ethers and bromination, the Wittig
More informationNeighbors of Catalytic anti-markovnikov Olefin Hydration: A Mechanistic Review
Neighbors of Catalytic anti-arkovnikov Olefin ydration: A echanistic eview anti-arkovnikov Wacker oxidation anti-arkovnikov alkyne hydration anti-arkovnikov hydroamination Scope of today s talk anti-arkovnikov
More informationTMSCl imidazole DMF. Ph Ph OTMS. Michael reaction. Michael reaction Ph R 3. epoxidation O R
eaction using diarylprolinol silyl ether derivatives as catalyst 1) C Et K C 3, ) MgBr, TF TMS hexane, 0 o C TBS p- C 6 4, T C Et 85%, 99% ee Angew. Chem., nt. Ed., 44, 41 (005). rg. Synth., 017, 94, 5.
More informationWhen something goes wrong. Goya: Mother showing her derformed child to two women Louvre, Paris
1 ew Catalytic Asymmestric eactions Karl Anker Jørgensen Danish ational eserach Foundation: Center for Catalysis Department of Chemistry, Aarhus University Denmark kaj@chem.au.dk When something goes wrong
More informationboth substrate : activated wastes derived from M and X one substrate : activated wastes derived from X
October 20th, 2007 Lit. Seminar Transition Metal Catalyzed Intermolecular ormations of - Bond : post-cross Coupling i) Cross Coupling reaction -M + '- -' (M = Zn, Sn, B,,,) ii) Direct ylation - + '- -'
More informationSynthetic Methodology. Using Tertiary Phosphines. as Nucleophilic Catalysts
Synthetic Methodology Using Tertiary osphines as Nucleophilic Catalysts 1 3 2 u 2 (P 3 ) 3 4 1 2 D. Ma, X. Lu 1988 1 2 Pd 2 (dba) 3.CCl 3 /P 3 /Ac or Pd(Ac) 2 /P 3 1 2 B. M. Trost 1988 1 3 2 u 2 (P 3 )
More informationElementary Organometallic Reactions
Elementary eactions CE 966 (Tunge) Elementary rganometallic eactions All mechanisms are simply a combination of elementary reactions. 1) Coordination -- issociation 2) xidative Addition -- eductive Elimination
More informationCatalysis by Group IV Elements CHEM 966 (Tunge) Good reference: Titanium and Zirconium in Organic Synthesis Ilan Marek Ed., 2002.
Catalysis by Group IV Elements CEM 966 (Tunge) Good reference: Titanium and Zirconium in rganic Synthesis Ilan Marek Ed., 2002. Electronegativity: Ti(1.54); (1.33); f(1.3) Much of the chemistry is dominated
More informationThree Type Of Carbene Complexes
Three Type f arbene omplexes arbene complexes have formal metal-to-carbon double bonds. Several types are known. The reactivity of the carbene and how it contributes to the overall electron counting is
More informationCatalytic Asymmetric Acyl Halide-Aldehyde Cyclocondensation Reactions of Substituted Ketenes
Catalytic Asymmetric Acyl Halide-Aldehyde Cyclocondensation eactions of Substituted Ketenes Scott G. elson, Cheng Zhu, and Xiaoqiang Shen J. Am. Chem Soc. 2004, 126, 14-15. Michael C. Myers, Literature
More informationAsymmetric Nucleophilic Catalysis
Asymmetric ucleophilic Catalysis Chiral catalyst X 2 Chiral catalyst X = alkyl, X 1 2 1 Vedejs, E.; Daugulis,. J. Am. Chem. Soc. 2003, 125, 4166-4173 Shaw, S. A.; Aleman,.; Vedejs, E. J. Am. Chem. Soc.
More informationCarbenes and Carbene Complexes I Introduction
Carbenes and Carbene Complexes I Introduction A very interesting (honest) class of radical-like molecules Steadily becoming more important as they find far more synthetic applications We will primarily
More informationSilica-Supported Cationic Gold(I) Complexes as Heterogeneous Catalysts for Regio- and Enantioselective Lactonization Reactions
Silica-Supported Cationic Gold(I) Complexes as Heterogeneous Catalysts for Regio- and Enantioselective Lactonization Reactions Xing-Zhong Shu, Son C. Nguyen,Ying He, Fadekemi Oba, Qiao Zhang, Christian
More informationA Stereoselective Synthesis of (+)-Gonyautoxin 3
A Stereoselective Synthesis of (+)-Gonyautoxin 3 Mulcahy, J. V.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 12630-12631 Total Synthesis of (+)-Lithospermic Acid by Asymmetric Intramolecular Alkylation via
More informationShort Literature Presentation 10/4/2010 Erika A. Crane
Copper-Catalyzed Enantioselective Synthesis of trans-1- Alkyl-2-substituted Cyclopropanes via Tandem Conjugate Additions-Intramolecular Enolate Trapping artog, T. D.; Rudolph, A.; Macia B.; Minnaard, A.
More informationChiral Bronsted Acids as Catalysts
Chiral Bronsted Acids as Catalysts Short Literature Seminar 6/3/08 Dustin aup BIL Derived osphoric Acids - First reported in 1992 as a ligand by irrung and coworkers. 4 h 2 irrung Tet. Lett. 1992, 33,
More informationCopper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group.
Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group. akatani, Y.; Koizumi, Y.; Yamasaki, R.; Saito, S. rg. Lett. 2008, 10, 2067-2070. An Annulation Reaction for the Synthesis
More informationOrganometallic Rections 1: Reactions at the Metal
E Organometallic Rections 1: Reactions at the Metal Three major classes of reactions: 1 Ligand Substitution associative (cf. S N 2) dissociative (cf. S N 1) interchange (not dealt with in this course)
More informationMechanism Problem. 1. NaH allyl bromide, THF N H
Mechanism Problem 1. a allyl bromide, TF 2. 9-BB (1.2 equiv), TF, rt; ame (1.2 equiv); t-buli (2.4 equiv), TMEDA (2.4 equiv) 30 to rt; allyl bromide; 30% 2 2, aq. a, 0 C (58% yield) Mechanism Problem 9-BB
More informationHomogeneous Gold Catalysis - Unique Reactivity for Activation of C C Multiple Bonds
1 rganic Seminar 2011.05.09 omogeneous Gold Catalysis - Unique Reactivity for Activation of C C Multiple Bonds ysical rganic Chemistry Laboratory (Nakamura Laboratory) D2 Masaki Sekine Development of Gold
More informationASYMMETRIC PALLADIUM-CATALYZED ALKENE CARBOAMINATION REACTIONS FOR THE SYNTHESIS OF CYCLIC SULFAMIDES
AYMMETIC PALLADIUM-CATALYZED ALKEE CABAMIATI EACTI F TE YTEI F CYCLIC ULFAMIDE Chem. Eur. J. 2016, 22, 5919 5922 Zachary J. Garlets, Kaia. Parenti, and John P. Wolfe James Johnson Wipf Group Current Literature
More informationOC 2 (FS 2013) Lecture 3 Prof. Bode. Redox Neutral Reactions and Rearrangements
C 2 (F 203) Lecture 3 Prof. Bode edox eutral eactions and earrangements Types of edox eutral rganic eactions. eactions with no external reducing or oxidizing agent In this case, one part of the starting
More informationSp 3 C-H Bond Activation Catalyzed by Transition Metal. Reporter: Wan Xiaobing Supervisor: Prof. Shi Zhangjie
Sp 3 C- Bond Activation Catalyzed by Transition Metal Reporter: Wan Xiaobing Supervisor: Prof. Shi Zhangjie Academic: high bond energy Practical: abundant, cheap, clean 2 hv C n 2n+2 Cl 2 C n 2n+2-m Cl
More informationIntramolecular Huisgen-Type Cyclization of Platinum-Bound Pyrylium Ions with Alkenes and Subsequent Insertion into a Benzylic C-H Bond
Intramolecular uisgen-type Cyclization of Platinum-Bound Pyrylium Ions with Alkenes and Subsequent Insertion into a Benzylic C- Bond Chang o h,* Ji o Lee, Su Jin Lee, Jae Il Kim, and Chang Seop ong Department
More informationSolvias (R)-MeO-BIPHEP Ligand Kit
metals inorganics organometallics catalysts ligands custom synthesis cgm facilities nanomaterials Catalog # 96-3655 Solvias ()- and (S)-Me BIE Ligand Kits for asymmetric hydrogenation and other catalytic
More informationChem 634. Introduction to Transition Metal Catalysis. Reading: Heg Ch 1 2 CS-B 7.1, , 11.3 Grossman Ch 6
Chem 634 Introduction to Transition etal Catalysis eading: eg Ch 1 2 CS-B 7.1, 8.2 8.3, 11.3 Grossman Ch 6 Announcements Problem Set 1 due Thurs, 9/24 at beginning of class ffice our: Wed, 10:30-12, 220
More informationTransition Metal-Catalyzed 1,2-Diamination of Alkenes. Group Meeting Timothy Chang
Transition Metal-Catalyzed 1,2-Diamination of Alkenes Group Meeting Timothy Chang 04-27-10 Valuable 1,2-Diamine Motif H H S Biotin CH H H Pt Eloxatin (Anticaner) H 2 AcH CHEt 2 Tamiflu (Antiviral) Et Ph
More informationChiral Catalysis. Chiral Catalyst. Substrate. Chiral Catalyst
Chiral Catalysis Chiral (stoichiometric) reagents are a very important class of compound but... eed a stoichiometric quantity of the chiral component Unless it is cheap or recoverable this is not very
More informationHighly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid
Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid Shiqing Xu, Akimichi Oda, Thomas Bobinski, Haijun Li, Yohei Matsueda, and Ei-ichi Negishi Angew. Chem. Int. Ed. 2015,
More informationSonogashira: in situ, metal assisted deprotonation
M.C. White, Chem 253 Cross-Coupling -120- Week of ctober 11, 2004 Sonogashira: in situ, metal assisted deprotonation catalytic cycle: ' (h 3 ) n d II The first report: h Sonogashira T 1975 (50) 4467. h
More informationManganese-Catalyzed Late- Stage Aliphatic C H Azidation
Wipf group current literature Manganese-Catalyzed Late- Stage Aliphatic C H Azidation J. Am. Chem. Soc. 2015, 137, 5300 5303 Xiongyi Huang, Tova M. Bergsten, and John T. Groves Department of Chemistry,
More informationOrganic Chemistry Laboratory Summer Lecture 6 Transition metal organometallic chemistry and catalysis July
344 Organic Chemistry Laboratory Summer 2013 Lecture 6 Transition metal organometallic chemistry and catalysis July 30 2013 Summary of Grignard lecture Organometallic chemistry - the chemistry of compounds
More informationHalogen Bond Applications in Organic Synthesis. Literature Seminar 2018/7/14 M1 Katsuya Maruyama
Halogen Bond Applications in Organic Synthesis Literature Seminar 2018/7/14 M1 Katsuya Maruyama 1 Contents 1. Introduction 2. Property of Halogen Bond 3. Application to Organic Synthesis 2 1. Introduction
More informationStable gold(iii) catalysts by oxidative addition of a carboncarbon
Stable gold(iii) catalysts by oxidative addition of a carboncarbon bond Chung-Yeh Wu, Takahiro oribe, Christian Borch Jacobsen & F. Dean Toste ature, 517, 449-454 (2015) presented by Ian Crouch Literature
More informationBranched-Regioselective Hydroformylation with Catalytic Amounts of a Reversibly Bound Directing Group
1/12 Branched-egioselective ydroformylation with Catalytic Amounts of a eversibly Bound Directing Group h(i)/me C/ 2 MS 4A branched major by Christian U. Grünanger and Bernhard Breit Angew. Chem. Int.
More informationChiral Proton Catalysis in Organic Synthesis. Samantha M. Frawley Organic Seminar September 14 th, 2005
Chiral Proton Catalysis in rganic Synthesis Samantha M. Frawley rganic Seminar September 14 th, 2005 Seminar utline Introduction Lewis Acid-assisted Chiral Brønsted Acids Enantioselective protonation for
More informationChiral Diol Promoted Boronates Addi3on Reac3ons. Lu Yan Morken Group Boston College
Chiral Diol Promoted Boronates Addi3on Reac3ons Lu Yan Morken Group Boston College Main Idea R R B or R R B Ar * exchange B * * or B Ar R 1 R 1 R 2 R 1 R 2 Products not nucleophilic enough nucleophilic
More informationProblem session (3) Daiki Kuwana. Please fill in the blank and explain reaction mechanisms and stereoselectivities.
Problem session (3) Daiki Kuwana Please fill in the blank and explain reaction mechanisms and stereoselectivities. 1. 1-1 1. (Ac) 2 (10 mol%), DPEphos (20 mol%) Et 3, toluene, 90 C 2. s 4 (14 mol%), M;
More informationPalladium-Catalyzed Alkylarylation of Acrylamides with
Supporting Information Palladium-Catalyzed Alkylarylation of Acrylamides with Unactivated Alkyl Halides Hua Wang, Li-a Guo, and Xin-Hua Duan* Department of Chemistry, School of Science and ME Key Laboratory
More informationUse of Cp 2 TiCl in Synthesis
Use of 2 TiCl in Synthesis eagent Control of adical eactions Jeff Kallemeyn May 21, 2002 eactions of 2 TiCl 1. Pinacol Coupling H H H 2. Epoxide pening H H E H Chemoselectivity Activated aldehydes (aromatic,
More informationWilkinson s other (ruthenium) catalyst
Wilkinson s other (ruthenium) catalyst Cl 3 ; 2 h 3, reflux 3h h 3 Cl h 3 h Cl 3 Good catalyst especially for 2 1-alkenes 2, base toluene Cl h 3 h 3 h 3 Et 3 Cl h 3 Cl h 3 h 3 R h 3 h 3 Cl h 3 R RC 2 C
More informationLiterature Report. Catalytic Enantioselective Synthesis of Isoindolinones through a Biomimetic Approach. : Zhong Yan : Ji Zhou :
Literature Report Catalytic Enantioselective Synthesis of Isoindolinones through a Biomimetic Approach Reporter Checker Date : Zhong Yan : Ji Zhou : 2017-12-22 Min, C.; Lin, Y.; Seidel, D. Angew. Chem.
More informationRecent advances in transition metal-catalyzed or -mediated cyclization of 2,3-allenoic acids: New methodologies for the synthesis of butenolides*
Pure Appl. Chem., Vol. 76, No. 3, pp. 651 656, 2004. 2004 IUPAC Recent advances in transition metal-catalyzed or -mediated cyclization of 2,3-allenoic acids: New methodologies for the synthesis of butenolides*
More informationAdditions to the Carbonyl Groups
Chapter 18 Additions to the Carbonyl Groups Nucleophilic substitution (S N 2andS N 1) reaction occurs at sp3 hybridized carbons with electronegative leaving groups Why? The carbon is electrophilic! Addition
More informationOrganocopper Reagents
rganocopper eagents General Information!!! why organocopper reagents? - Efficient method of C-C bond formation - Cu less electropositive than Li or Mg, so -Cu bond less polarized - consequences: 1. how
More informationOxidative Addition and Reductive Elimination
xidative Addition and Reductive Elimination red elim coord 2 ox add ins Peter.. Budzelaar xidative Addition Basic reaction: n + X Y n X Y The new -X and -Y bonds are formed using: the electron pair of
More informationAsymmetric Synthesis of Medium-Sized Rings by Intramolecular Au(I)-Catalyzed Cyclopropanation
Asymmetric Synthesis of Medium-Sized ings by Intramolecular Au(I)-Catalyzed Cyclopropanation 1 2 Iain D. G. Watson, Stefanie itter, and F. Dean Toste JACS, ASAP, 1/22/2009 DI: 10.1021/ja8085005 2.5 mol%
More informationOrganometallic Chemistry and Homogeneous Catalysis
Organometallic Chemistry and Homogeneous Catalysis Dr. Alexey Zazybin Lecture N6 Kashiwa Campus, November 27, 2009 Group VIB: Cr, Mo, W -Oxidation states from -2 to +6 -While +2 and +3 for Cr are quite
More informationJACS ASAP Article: Published 3/12/08. Lei Jiao, Changxia Yuan and Zhi-Xiang Yu. Current Literature: 3/29/08. David Arnold
Tandem h(i)-catalyzed [(5+2)+1] Cycloaddition/Aldol eaction for the Construction of Linear Triquinane Skeleton: Total Syntheses of (+)-irsutene and (+)-1- Desoxyhypnophilin JACS ASAP Article: Published
More informationMetallocenes WILEY-VCH. Volume 2. Synthesis Reactivity Applications. Edited by Antonio Togni and Ronald L. Halterman
Metallocenes Volume 2 Synthesis Reactivity Applications Edited by Antonio Togni and Ronald L. Halterman WILEY-VCH Weinheim New York Chichester Brisbane Singapore Toronto / Preface V Volume 1 Synthesis
More informationCHO. OMe. endo. xylene, 140 o C, 2 h 70% 1. CH 2 (OMe) 2, MeOH TsOH, rt 2. Bu 2 O, 1,2-dichloroethane 140 o C, 2 h 3. 6 M HCl, THF, rt 44%
VII Abstracts 2010 p1 2.4.12 Arene rganometallic Complexes of Chromium, Molybdenum, and Tungsten M. Uemura This review is an update to Section 2.4 and covers the literature from 1999 to 2010. (h 6 -Arene)chromium
More informationNon-Metathesis Ruthenium-Catalyzed Reactions for Organic Synthesis
on-tathesis thenium-catalyzed eactions for rganic Synthesis Tristan Lambert MacMillan Group eting May 23, 2002 I. Properties of thenium II. eductions III. xidations IV. Isomerizations V. C-C bond forming
More informationStudies on Heck and Suzuki Reactions Catalyzed by Palladium(0) and Wacker- Type Oxidative Cyclization Catalyzed by Palladium(II)
Studies on eck and Suzuki Reactions Catalyzed by Palladium(0) and Wacker- Type xidative Cyclization Catalyzed by Palladium() Zuhui Zhang enmark Group Meeting 10/21/2008 1 Part ne: Palladium(0)-Catalyzed
More informationNine-Step Enantioselective Total Synthesis of (+)-Minfiensine
ine-step nantioselective Total Synthesis of (+)-Minfiensine Jones, S. B.; Simmons, B.; MacMillan, D. W. C.* J. Am. Chem. Soc. 2009, ASAP. DI: 10.1021/ja906472m Kara George Wipf Group - Current Literature
More informationπ-alkyne metal complex and vinylidene metal complex in organic synthesis
Literature Seminar 080220 Kenzo YAMATSUGU (D1) π-alkyne metal complex and vinylidene metal complex in organic synthesis 0. Introduction ' ' = π-alkyne metal complex vinylidene metal complex ecently, electrophilic
More informationLiterature Report 3. Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A. Date :
Literature Report 3 Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A Reporter : Xiao-Yong Zhai Checker : Shubo u Date : 2017-10-30 Pritchett, B. P.; Donckele, E. J.; Stoltz, B. M. Angew.
More informationsp 3 C-H insertion by α-oxo Gold Carbene B4 Kei Ito
1 sp 3 C-H insertion by α-oxo Gold Carbene B4 Kei Ito 2016. 1. 30 1. Introduction 2 About Carbene 3 Brief history of carbene (~2000) Carbene Neutral compounds featuring a divalent carbon atom with only
More informationCatalytic Asymmetric Intramolecular. Reactions
Catalytic Asymmetric Intramolecular Pauson-Khand and Pauson-Khand-Type eactions Steven Ballmer CEM 535 Seminar ctober 9, 2008 University of Illinois at Urbana-Champaign pyright 2008 by Steven Ballmer Synthetic
More informationOrgano-transition Metal Chemistry
Prof. Dr. Burkhard König, nstitut für rganische Chemie, Universität egensburg 1 rgano-transition tal Chemistry 1. Some Basics Chemistry involves intermediates containing transition-metal carbon bonds tal-carbon
More informationCobalt Catalysed Organic Reactions
Department of Chemistry and Biochemistry, University of Bern Topic review Cobalt Catalysed Organic Reactions Group of Prof. Philippe Renaud Andrey S. Kuzovlev 29.01.2015 ... we invite the attention of
More information