Review. Recent Developments in Pd-catalyzed Carbonylation Reaction. Li Yuanhe. Supervisors: Prof. Yang Prof. Chen Prof. Tang
|
|
|
- Jason Kelley
- 5 years ago
- Views:
Transcription
1 Review Recent Developments in Pd-catalyzed Carbonylation Reaction Li Yuanhe Supervisors: Prof. Yang Prof. Chen Prof. Tang
2 History 1962, E. Fischer Z. Nafurforsch. 1962, 17b, , R. Heck J. Org. Chem. 1972, 37(14), , Heck reaction 1974, R. Heck J. Org. Chem. 1974, 39(23), /39
3 Mechanism Migration or Insertion? Assume: No trans-insertion No stereo-wobbling 3/39
4 Mechanism Migration or Insertion? K. Noack And F. Calderazzo, J. Organometal. Chem. 1967, 10, /39
5 Mechanism Migration or Insertion? B. Scott Williams, et. al., Organometallics 2009, 28, Exception Gordon. K. Anderson, et. al., Acc. Chem. Res. 1984,17, /39
6 Mechanism Mostly dissociation-insertion (3/4-coordinate, not 4/5) Non-RDS fast process Kinetic study of >100 rxn of Ni, Pd, Pt. R.F. Heck, et. al., J. Am. Chem. Soc., 1976, 98, Exception Excessed or firm ligands C.H. Stam, et. al., Inorg. Chim. Acta, 1990, 169, 5. 6/39
7 Influencing factors CO substitution Electronic migrating R Nucleophilicity CO Pressure Sterically hindered P t Bu 3, BuPAd 2, bulky NHC Throw-away ligend (L) Py, MeCN > PR 3 > AcO -, Cl - R: n-alkyl anion > allylic, benzylic Ar: electron rich > electron poor Trans effect on R Trapping ligand Trans-effect / Pi-pushing effect Electronic CO δ + CO Ion effect: Li + > Na + Lewis acid Favor strong coordination ligand PMe 3 > PMe 2 Ph > PMePh 2 > CO Nucleophile / Bidentate ligand Binding angle Edward S. Petrov, et. al., React. Kinet. Catal. Lett., 1998, 64, 359. S. Sakaki, et.al., J. Am. Chem. Soc. 1983, 105, Kingsley J. Cavel, Coord. Chem. Rev. 1996, 155, 209. Tao Tu, et.al., Synthesis 2014, 46, /39
8 Outline Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation - Carbonylation 8/39
9 Outline Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation - Carbonylation 9/39
10 C(sp) Pd Takahashi, T. et. al., Tetrahedron Lett. 1980, 21, 849. Takahashi, T. et. al., Tetrahedron Lett. 1980, 21, 849. Ishii, Y et. al.,. Tetrahedron Lett. 1999, 40, Ishii, Y et. al.,. Tetrahedron Lett. 1999, 40, /39
11 Outline Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation - Carbonylation 11/39
12 C(sp 2 ) Pd 12/39
13 C(sp 2 ) Pd Cowell, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 卿凤翎, et.al. J. Fluorine Chem. 2002, 114, 177. Hamel, N. et. al., Tetrahedron Lett. 1987, 28, Ban, Y. et. al., J. Chem. Soc., Chem. Commun. 1979, 698. Ban, Y. et. al., Tetrahedron 1985, 41, /39
14 C(sp 2 ) Pd Chiusoli, G. P. et. al., J. Chem. Soc., Perkin Trans , 147. Norton, J. R. et. al., J. Am. Chem. Soc. 1981, 103, Dupont, J. et. al., Tetrahedron Lett. 2002, 43, 753. 赵世民, et. al., J. Org. Chem. 2005, 70, /39
15 C(sp 2 ) Pd Hirao, T. et. al., J. Org. Chem. 1997, 62, Gabriele, B. et. al.,; Adv. Synth. Catal. 2004, 346, 351. Gabriele, B. et. al., Synthesis 2007, /39
16 C(sp 2 ) Pd Larock, R. C. et. al., J. Org. Chem. 2004, 69, BILN 2061 Haddad, N.; Tan, J.; Farina, V. J. Org. Chem. 2006, 71, /39
17 Outline Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation - Carbonylation 17/39
18 C(sp 3 )-Pd Danishefsky, S. et. al.; Tetrahedron Lett. 1983, 24, 15. Yoshida, Z. et. al., J. Am. Chem. Soc. 1988, 110, Danishefsky, S et. al.; Tetrahedron Lett. 1983, 24, 15. Yoshida, Z. et. al., J. Am. Chem. Soc. 1988, 110, /39
19 C(sp 3 )-Pd Ilhyong Ryu, et. al., Acc. Chem. Res. 2014, 47, /39
20 Beyond small ring Cao, H.; Vieira, T. O. et. al.,; Alper, H. Org. Lett. 2011, 13, 11. Chouhan, G.; Alper, H. et. al., Org. Lett. 2010, 12, 192. Lenoble, G.; Urrutigoity, M.; Kalck, P. et. al., Tetrahedron Lett. 2001, 42, /39
21 Outline Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation Carbonylation Outlook 21/39
22 Double Carbonylation Aklo Yamamoto, et. al., Tetrahedron Lett., 1982, 23, ; J. Am. Chem. Soc., 1985, 107, M. Tanaka, et. al., J. Organomet. Chem., 1982, 233, C64 C66. (11 days later) 22/39
23 Double Carbonylation T. Watanabe, et. al., J. Org. Chem., 2001, 66, /39
24 Double Carbonylation Yoshinori Kondo, et. al., Chem. Commun., 2006, /39
25 Double Carbonylation Takashi Takahashi, et. al., Tetrahedron, 2015, 71, /39
26 Outlook Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation Carbonylation Outlook 26/39
27 C-H Carbonylation Alkoxycarbonylation Aryl C(sp 2 )-H Booker-Milburn, K. I., Angew. Chem., Int. Ed. 2009, 48, Shi, Z.-J. Dalton Trans. 2010, 39, /39
28 C-H Carbonylation Lei, A.-W. Chem. Eur. J. 2011, 17, 李福伟, et.al. Org. Lett. 2012, 14, /39
29 C-H Carbonylation Yu, J.-Q. Chem. Sci. 2011, 2, Shi, B.-F. Synlett. 2013, 24, Shi, B.-F. Org. Biomol. Chem. 2014, 12, Shih-Ching Chuang, Chem. Commun. 2013, 49, /39
30 C-H Carbonylation Huang, H. ( 黄汉民 ) J. Am. Chem. Soc. 2012, 134, Huang, H., et. al. Org. Lett., 2013, 15 (13), /39
31 C-H Carbonylation Inert C(sp3)-H carbonylation Fujiwara, Y., et. al. Chem. Lett. 1989, Fujiwara, Y., et. al. Chem. Lett. 1992, 1141 Fujiwara, Y., et. al. Organomet. Chem. 1994, 473, 329. Fujiwara, Y., et. al. Chem. Lett. 1991, 1433 Fujiwara, Y., et. al. Org. Lett. 1999, /39
32 C-H Carbonylation Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, Matthew J. Gaunt, Nature 2014, 510, /39
33 C-H Carbonylation Xi-Sheng Wang, Org. Lett. 2015, 17, /39
34 Outline Equivalent intermediate C(sp) Pd C(sp 2 ) Pd C(sp 3 ) Pd Double Carbonylation C-H Activation Carbonylation Outlook All carbon skeleton / ring system 34/39
35 All carbon skeleton Arcadi, A.; Cacchi, S.; Fabrizi, G.; Moro, L. Eur. J. Org. Chem. 1999, Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, Y. Zhao, L. Jin, P. Li, A. Lei, J. Am. Chem. Soc. 2008, 130, /39
36 All carbon skeleton Beller, M. Chem. Asian J. 2012, 7, S.-C. Choi, Synth. Commun. 2001, 31, Hiroaki Sasai, et. al., Synlett 2009, R. F. W. Jackson, J. Chem. Soc. Perkin Trans , /39
37 All carbon ring system Wolfgang Oppolzer, et. al., Helvetica Chimica Acta, 1991, 74, 465 By Dr. You Lin, 2012 Jiahua Chen, and Zhen Yang, et. al., Org. Lett. 2005, 7, Jia-Hua Chen, Aiwen Lei, Zhen Yang, et..al., Synthesis, 2007, 16, Zhen Yang, and Yun-Dong Wu, et. al., J. Org. Chem. 2009, 74, /39
38 All carbon ring system Other examples? Why rare? Chuangchuang Li, and Zhen Yang, Chem. Asian J. 2013, 8, /39
39 Acknowledgements Prof. Yang, Prof. Chen, Prof. Tang Mr. You Lin B630 Everyone in Lab. and everyone here Ac 39/39
40 Supplement Lenoble, G.; Urrutigoity, M.; Kalck, P. Tetrahedron Lett. 2001, 42, 3697 Yu Bai, Dexter C. Davis, and Mingji Dai, Angew. Chem. Int. Ed. 2014, 53, /39
41 Regioselectivity of Allene Cyclocarbonylation Selective allylic substitution at more substituted site Ye, F.; Alper, H. J. Org. Chem. 2007, 72, Richard C. Larock* and John M. Zenner, J. Org. Chem. 1995, 60, /39
42 Sequence Selectivity Larock, R. C. J. Org. Chem. 2004, 69, Yang, Q.; Alper, H. J. Org. Chem. 2010, 75, 948. Xuefeng Jiang*, et. al., Angew. Chem. Int. Ed. 2015, 54, /39
A 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
Review. Frank Glorius & His Rh(III) C-H Activation. Li Yuanhe. Supervisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo 1 /21
Review Frank Glorius & His Rh(III) C-H Activation Li Yuanhe Supervisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo 1 /21 Author Introduction Prof. Dr. Frank Glorius 1972 Born 1991-1992 Military service
C H activation of aliphatic amines without unnecessary mask M2 Takaya Togo
C H activation of aliphatic amines without unnecessary mask 2017.11.25 M2 Takaya Togo 1 Outline 1.Introduction 2.Free amines as DG Discovery of new activation mode Mechanistic studies Application of the
Oxidative 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,
Catellani 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
N-Heterocyclic Carbene Catalysis via Azolium Dienolates: An Efficient Strategy for Enantioselective Remote Functionalizations
Angew. Chem. Int. Ed. 2017, 10.1002. 1 N-Heterocyclic Carbene Catalysis via Azolium Dienolates: An Efficient Strategy for Enantioselective Remote Functionalizations Reporter: En Li Supervisor: Prof. Yong
Recent Developments in Alkynylation
--New approaches to introduce an alkynyl group Reporter: Zhao-feng Wang Supervisor: Yong Huang 2013-03-27 Contents 1. Introduction of Acetylene Chemistry 2. Nucleophilic alkynylation : Classic text book
sp 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
Rh(III)-catalyzed C-H Activation and Annulation via Oxidizing Directing Group. Lei Zhang 03/23/2016 Dong Group
Rh(III)-catalyzed C-H Activation and Annulation via Oxidizing Directing Group Lei Zhang 03/23/2016 Dong Group Content 1 Alkyne involved Annulation in Hua group 2 3 4 Brief Introduction of Internal Oxidants
Cambrian Explosion, Complex Eukaryotic Organism, Ozonosphere 3
Reporter: Wang Yuefan Reporter: Wang Yuefan Supervisor: Prof. Yang Zhen Supervisor: Prof. Yang Zhen Prof. Chen Jiahua Prof. Chen Jiahua 1 2011-12-2727 2011-02 2012-03 02-25 03-23 25 Content Preface Nature
Modern Synthetic Methods
Modern Synthetic Methods Dr. Dorian Didier dodich@cup.uni-muenchen.de Functionnalized Organometallic Reagents C-N, C-O and C-S Bond Formation Introduction to Organoboron Chemistry Introduction to Organosilicon
Review Revisiting the Baldwin s Rules Guidelines for Ring Closure Li Yuanhe Anion- 3/4 4/5 5/6 6/7 endo- -dig exo- endo- -trig exo- endo- -tet exo-
Review Revisiting the Baldwin s Rules Guidelines for Ring Closure Li Yuanhe Anion - 3/4 4/5 5/6 6/7 -trig Supervisors: Prof. Yang Prof. Chen -tet Prof. Tang Introduction (Sir) Jack Baldwin 1938, Born,
Selectivity and Natural Product Synthesis. Reporter: Liang Xin-ting Supervisors: Prof. Yang Prof. Chen Prof. Tang
Selectivity and Natural Product Synthesis Reporter: Liang Xin-ting Supervisors: Prof. Yang Prof. Chen Prof. Tang Content Introduction Selectivity of oxidative coupling Chemoselectivity Regioselectivity
Alkyne Dicobalt Complexes in Organic Chemistry
Alkyne Dicobalt Complexes in Organic Chemistry Sun Baochuan Supervisors: Prof. Yang Prof. Chen Prof. Tang Cobalt - Co From German word kobald - evil spirits Atomic Number: 27 Group: 9 Period: 4 3d 7 4s
Copper-Catalyzed Aerobic Oxidative C-H Functionalizations. Supervisor: Prof. Yong Huang Reporter: Weiyu Yin ( 殷韦玉 ) Date:
Copper-Catalyzed Aerobic Oxidative C-H Functionalizations Supervisor: Prof. Yong Huang Reporter: Weiyu Yin ( 殷韦玉 ) Date: 2013-04-08 0 Content Introduction C-H Oxidation Initiated by Single-Electron Transfer(SET)
C 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
The Chemistry of Organozinc Reagent a long story. Reporter: Han Yixin Adivisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo Date: Nov. 22 nd.
The Chemistry of Organozinc Reagent a long story Reporter: Han Yixin Adivisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo Date: Nov. 22 nd. 2013 2 Content Introduction Reactions of Organozinc reagent
Metalloporphyrin. ~as efficient Lewis acid catalysts with a unique reaction-field~ and. ~Synthetic study toward complex metalloporphyrins~
Metalloporphyrin ~as efficient Lewis acid catalysts with a unique reaction-field~ and ~Synthetic study toward complex metalloporphyrins~ Literature Seminar Kenta Saito (D1) 1 Topics Chapter 1 ~as efficient
Self-stable Electrophilic Reagents for Trifluoromethylthiolation. Reporter: Linrui Zhang Supervisor: Prof. Yong Huang Date:
Self-stable Electrophilic Reagents for Trifluoromethylthiolation Reporter: Linrui Zhang Supervisor: Prof. Yong Huang Date: 2017-12-25 Content Introduction Trifluoromethanesulfenates: Preparation and reactivity
Story Behind the Well-Developed Chiral Lewis Acid in Asymmetric Diels-Alder reaction
Story Behind the Well-Developed Chiral Lewis Acid in Asymmetric Diels-Alder reaction Reporter: Zhang Sulei Supervisors: Prof. Yang Zhen Prof. Chen Jiahua Prof. Tang Yefeng 2015-10-05 1 Contents Background
A Tandem Semipinacol Rearrangement/Alkylation of a-epoxy Alcohols: An Efficient and Stereoselective Approach to Multifunctional 1,3-Diols
A Tandem Semipinacol Rearrangement/Alkylation of a-epoxy Alcohols: An Efficient and Stereoselective Approach to Multifunctional 1,3-Diols B() 2 H H B() 2 H H Hu, X.-D.; Fan, C.-A.; Zhang, F.-M.; Tu, Y.
Organic Reactions catalyzed by rhenium carbonyl complexes
Organic Reactions catalyzed by rhenium carbonyl complexes Fanyang Mo Dong group seminar Feb. 26, 2014 Ref: Kuninobu, Y.; Takai, K. Chem Rev. 2011, 111, 1938. 1 Accidentally found by Ogawa in 1908, and
sp 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)
Palladium-catalyzed sp 3 C H activation. Yan Xu Dong Group Meeting Apr. 2, 2014
Palladium-catalyzed sp 3 C H activation, Yan Xu Dong Group Meeting Apr. 2, 2014 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common sp 3 C H activation:
Enantioselective 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
Course 201N 1 st Semester Inorganic Chemistry Instructor: Jitendra K. Bera
andout-9 ourse 201N 1 st Semester 2006-2007 Inorganic hemistry Instructor: Jitendra K. Bera ontents 3. rganometallic hemistry xidative Addition, Reductive Elimination, Migratory Insertion, Elimination
The Vinylogous Aldol Reaction
The Vinylogous Aldol Reaction Reporter: Sixuan Meng Supervisor: Prof. Huang 2013-09-09 Zanardi, F. et al. Chem. Rev. 2000, 100, 1929 Zanardi, F. et al.. Chem. Rev. 2011, 111, 3076 Introduction 2 3 Regiochemical
Rachel Whittaker Dong Group Literature Talk October 10, Ref: Perez-Temprano, M.H, Casares, J.A., Espinet, P., Chem. Eur. J. 2012, 18, 1864.
Rachel Whittaker Dong Group Literature Talk October 10, 2013 Ref: Perez-Temprano, M.H, Casares, J.A., Espinet, P., Chem. Eur. J. 2012, 18, 1864. Overview Introduction Group Exchange C-C Bond Forming Reactions
Synthetically useful extrusion reactions in organic chemistry
Synthetically useful extrusion reactions in organic chemistry Reporter: Sun Baochuan Supervisors: Prof. Yang Zhen Prof. Chen Jiahua Extrusion Reactions Extrusion Reaction: An atom or group Y connected
Xuefeng Jiang Professor Education Academic Career Awards International Invited Lecture USA Germany Shanghai Taiwan Singapore)
Xuefeng Jiang( 姜雪峰 ) Professor East China Normal University, 200062, Shanghai, China Tel: +86-21-52133654 E-mail: xfjiang@chem.ecnu.edu.cn Web: http://faculty.ecnu.edu.cn/s/641/main.jspy Education 1999-2003
Rhodium Catalyzed Alkyl C-H Insertion Reactions
Rhodium Catalyzed Alkyl C-H Insertion Reactions Rh Rh Jeff Kallemeyn 5/17/05 1. Cyclopropanation The Versatile and Reactive Rhodium Carbene R + Et Rh 2 (Ac) 4 R C 2 Et N 2 2. [2,3] sigmatropic rearrangement
Nickel-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](/thumbs/77/74720708.jpg "Nickel-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.
Recent 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*
Metal Hydrides, Alkyls, Aryls, and their Reactions
Metal Hydrides, Alkyls, Aryls, and their Reactions A Primer on MO Theory σ-bonding in Organotransition Metal Complexes M-C Bond Energies in Organotransition Metal Complexes Thermodynamic Predictions
Chromium Arene Complexes
Go through Reviews Chem. Reviews Chem. Soc. Reviews Book by Prof. A. J. Elias Chromium Arene Complexes Complexation of Cr(CO) 3 with ARENES Chromium arene complexes Metal complexation is appealing in organic
Curriculum Vitae Lingkui Meng
Curriculum Vitae Lingkui Meng E-mail: meng.lingkui@d.mbox.nagoya-u.ac.jp Phone/Fax: 052-789-5916 Current Appointments PostDoc, MEXT Project of Integrated Research on Chemical ynthesis, Nagoya University
Bifunctional 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
Complex Interactions of Pillar[5]arene with Paraquats and. Bis(pyridinium) Derivatives
![Complex Interactions of Pillar[5]arene with Paraquats and. Bis(pyridinium) Derivatives](/thumbs/94/119880372.jpg "Complex Interactions of Pillar[5]arene with Paraquats and. Bis(pyridinium) Derivatives")
Electronic supplementary information Complex Interactions of Pillar[5]arene with Paraquats and Bis(pyridinium) Derivatives Chunju Li,* Qianqian Xu, Jian Li, Feina Yao and Xueshun Jia* Department of Chemistry,
Use 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,
Construction of C-C or C-N Bond via C-H Activation ~Chemistry of Yong-Qiang Tu~
Literature Seminar 2010.5.26 Yao u(2) Construction of C-C or C-N Bond via C-H Activation ~Chemistry of Yong-Qiang Tu~ Contents: 1. Yong-Qiang Tu's Profile 2.LatestWorkofProfessorTu 2-1. C-H Activation
Strained 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
Nucleophilic 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)
Ligand Effects in Nickel Catalysis. Anthony S. Grillo Chem 535 Seminar October 22, 2012
Ligand in Nickel Catalysis Anthony S. Grillo Chem 535 Seminar October 22, 2012 Transition Metals in Chemistry Organotransition Metal Chemistry, Hartwig, J. F. University Science Books: Mill Valley, CA,
Beyond Directing Groups
Beyond Directing Groups Transition-Metal-Catalyzed C-H Activation of Simple Arenes Reporter: Huan Sun Supervisor: Yong Huang 2013-01-07 N. Kuhl, M. N. Hopkinson, J. W. Delord, F. Glorius, Angew. Chem.
C H Bond Functionalization: New Strategies for the Synthesis of Complex Natural Products and Pharmaceuticals. Phil Knutson Ferreira Group 12/3/2015
C H Bond Functionalization: New Strategies for the Synthesis of Complex Natural Products and Pharmaceuticals Phil Knutson Ferreira Group 12/3/2015 New strategies in organic synthesis nsf-cchf.com What
Protecing-Group-Free Synthesis. Reporter: Zhu Zhiyang Advisor: Prof Yang Prof Chen Prof Tang Date:
Protecing-Group-Free Synthesis Reporter: Zhu Zhiyang Advisor: Prof Yang Prof Chen Prof Tang Date: 2015.05.19 1 Outline Introduction Protecting-Group-Free Synthesis Historic Background Strategies & examples
Oxidative Addition/Reductive Elimination 1. Oxidative Addition
Oxidative Addition Oxidative Addition/Reductive Elimination 1 An oxidative addition reaction is one in which (usually) a neutral ligand adds to a metal center and in doing so oxidizes the metal, typically
Recent Developments in the Chemistry of Polyvalent Iodine Compounds
Recent Developments in the Chemistry of Polyvalent Iodine Compounds Jiang Zhongping 2005-9-23 Content I. Introduction II. Iodine(III) Compounds III. Iodine(V) Compounds IV. Conclusions Introduction Why
Iron Catalysed Coupling Reactions
LONG LITERATURE REPORT Iron Catalysed Coupling Reactions Mingyu Liu 2017. 8. 31 1 Fe [Ar]3d 6 4s 2 The fourth most common element in the Earth s crust Relatively less understanding and manipulation of
Chapter 2 The Elementary Steps in TM Catalysis
hapter 2 The Elementary Steps in TM atalysis + + ligand exchange A oxidative addition > n + A B n+2 reductive elimination < B n n+2 oxidative coupling + M' + M' transmetallation migratory insertion > (carbo-,
Asymmetric Palladium Catalyzed Cross-Coupling Reactions. Topic Talk September 4 th, 2014 Morken Lab Emma Edelstein 1
Asymmetric Palladium Catalyzed Cross-Coupling Reactions Topic Talk September 4 th, 2014 Morken Lab Emma Edelstein 1 Palladium Catalyzed Cross-Coupling Reactions 2 Kumada/Negishi Cross-Coupling Kumada:
Highly selective synthetic organic reactions utilizing cleavage of C-Cl bond
Highly selective synthetic organic reactions utilizing cleavage of C- bond SmI 2 Reformatsky rg. Lett. 2008, 10, 5453.) C- C-C C- C-C C- C-- C- Chem. Lett. 2009, 38, 1078. Sc(Tf) 3 (Chem. Lett. 2010, 39,
Tautomerism and Keto Enol Equilibrium
Tautomerism and Keto Enol Equilibrium Enols & enolates are important nucleophiles in organic & biochemistry. Keto-Enol Equilibrium: Tautomerisation can be catalyzed by either acids or bases. Relative stability
1. Theoretical Investigation of Mechanisms and Stereoselectivities of Synthetic Organic Reactions
1. Theoretical Investigation of Mechanisms and Stereoselectivities of Synthetic Organic Reactions 2. Copper Catalyzed One-Pot Synthesis of Multisubstituted Quinolinones Hao Wang Denmark Group Presentation
Lecture 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
Chem 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
Substitution and Elimination reactions
PART 3 Substitution and Elimination reactions Chapter 8. Substitution reactions of RX 9. Elimination reactions of RX 10. Substit n/elimin n of other comp ds 11. Organometallic comp ds 12. Radical reactions
Insertion Reactions. 1) 1,1 insertion in which the metal and the X ligand end up bound to the same (1,1) atom
Insertion Reactions xidative addition and substitution allow us to assemble 1e and 2e ligands on the metal, respectively. With insertion, and its reverse reaction, elimination, we can now combine and transform
Palladium-Catalyzed Oxidation of Alcohols by Molecular Oxygen: Recent Computational Insights. Presented by Dice
Palladium-Catalyzed Oxidation of Alcohols by Molecular Oxygen: Recent Computational Insights Presented by Dice OUTLINE Background Palladium Catalyst Systems for aerobic oxidation 1. Pd(OAc) 2 / DMSO Catalyst
VI. 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.
Mechanism of the oxidative addition of aryl halides to bis-carbene palladium(0) complexes*
Pure Appl. Chem., Vol. 82, No. 7, pp. 1393 1402, 2010. doi:10.1351/pac-con-09-09-22 2010 IUPAC, Publication date (Web): 4 May 2010 Mechanism of the oxidative addition of aryl halides to bis-carbene palladium(0)
KOtBu: A single electron donor? Reporter: Qiqiang Xie June 21, 2016
KtBu: A single electron donor? Reporter: Qiqiang Xie June 21, 2016 Content 2 Introduction Transition metal-free cross coupling reactions Reductive fragmentation of dithianes S R 1 reactions in DMF Summary
Short 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.
Direct α-arylation of Ketones
Direct α-arylation of Ketones Zhensheng Ding January 29, 2003 Department of Chemistry Michigan State University Direct α-arylation of Ketone Outline Introduction Mechanistic Study Factors Influencing the
The Synthesis of Molecules Containing Quaternary Stereogenic Centers via the Intramolecular Asymmetric Heck Reaction
The Synthesis of Molecules Containing Quaternary Stereogenic Centers via the Intramolecular Asymmetric Heck Reaction Reported by Eric P. Gillis April 19, 2007 INTRODUCTION The enantioselective synthesis
Supporting Information Metal-mediated and Metal-catalyzed Reactions of Isocyanides
Supporting Information Metal-mediated and Metal-catalyzed Reactions of Isocyanides Vadim P. Boyarskiy*, Nadezhda A. Bokach*, Konstantin V. Luzyanin*, Vadim Yu. Kukushkin* Institute of Chemistry, Saint
Aza-Wacker-Type Cyclization. Group Meeting Tuesday, April 19, 2011 William Kuester
Aza-Wacker-Type Cyclization Group Meeting Tuesday, April 19, 2011 William Kuester N-heterocylization Reductive Amination Hydroamination Oxidative Cyclization Chemler, S.R. Org. Biomol. Chem. 2009, 7, 3009-3019.
Anti-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
O CH 3. Mn CH 3 OC C. 16eelimination
igratory Insertion igratory Insertion/Elimination 1 A migratory insertion reaction is when a cisoidal anionic and neutral ligand on a metal complex couple together to generate a new coordinated anionic
The Mechanism of Pd-Catalyzed Amination Controversy.. And Conclusion?
The chanism of d-catalyzed Amination Controversy.. And Conclusion? R H R1 R 2 d(dba) 2 BIA, h R R1 R 2 Steve Tymonko SED Group eting 5/9/06 d-catalyzed Amination- Tin Initial Report- Kosugi, 1983 n-bu
The Development of Carbonyl- Olefin Metathesis. Li Zheng Dr. Wulff s Group 11/23/2016
The Development of Carbonyl- Olefin Metathesis Li Zheng Dr. Wulff s Group 11/23/2016 1 Metathesis AB + CD AC + BD http://msn.huanqiu.com/photo/gallery/2012-11/2671259.html http://edu.sina.com.cn/en/2013-07-10/152075337.shtml
Bo Yang Nov. 18 th, 2009
Bo Yang ov. 18 th, 2009 1 utline Introduction Traditional Stepwise Synthesis Approach ne-pot Synthesis Approach Conclusions 2 Importance of Fused Ring Structures Kubo, K. et al. Chem. Phram. Bull. 1979,
Nucleophilic Heterocyclic Carbene Catalysis. Nathan Werner Denmark Group Meeting September 22 th, 2009
Nucleophilic Heterocyclic Carbene Catalysis Nathan Werner Denmark Group Meeting September 22 th, 2009 Thiamine Thiamine Vitamin B 1 The first water-soluble vitamin described Is naturally synthesized by
Palladium-catalyzed cross-addition of triisopropylsilylacetylene to unactivated alkynes*
Pure Appl. Chem., Vol. 80, No. 5, pp. 1161 1166, 2008. doi:10.1351/pac200880051161 2008 IUPAC Palladium-catalyzed cross-addition of triisopropylsilylacetylene to unactivated alkynes* Naofumi Tsukada, Satoshi
Supporting Information. Cobalt Molybdenum Oxide Derived High-Performance Electrocatalyst
Supporting Information Cobalt Molybdenum Oxide Derived High-Performance Electrocatalyst for the Hydrogen Evolution Reaction Mingjie Zang, [a] Ning Xu, [a] Guoxuan Cao, [a] Zhengjun Chen, [a] Jie Cui, [b]
Recent Advances in C-B Bond Formation through a Free Radical Pathway
Recent Advances in C-B Bond Formation through a Free Radical Pathway G. Yan. D. Huang, X. Wu, Adv. Synth. Catal. 2017, 359, 188. Daniel Meyer University of Bern 18.01.2018, Topic Review Classical Methodes
Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C H Borylation
Enabled by Ligand-Controlled C H Borylation Yu Feng, Dane Holte, Jochen Zoller, Shigenobu Umemiya, Leah R. Simke, and Phil S. Baran J. Am. Chem. Soc. 2015, 137, 10160 10163. I. Introduction II. Retrosynthetic
Grob Fr agmentations. Dan Tao Overman Group Meeting 9/24/12
: Grob Fr agmentations Dan Tao Overman Group Meeting 9/24/12 What is a Grob Fragmentation? Heterolytic fragmentation is certain combinations of carbon and hetero atoms which undergo a regulated cleavage
Metal-catalyzed Carbonylation Reactions : No Need for Carbon Monoxide. Literature Seminar Benjamin Ovadia
Metal-catalyzed Carbonylation Reactions : No Need for Carbon Monoxide Literature Seminar 2017.08.26 Benjamin Ovadia 1 M-Catalyzed Carbonylative Coupling Pioneering work by Heck in the 70s Pd-Catalyzed
Palladium-Catalyzed Alkylation of sp2 and sp3 C-H Bonds with Methylboroxine and Alkylboronic Acids: Two Distinct C-H Activation Pathways
Palladium-Catalyzed Alkylation of sp2 and sp3 C-H Bonds with Methylboroxine and Alkylboronic Acids: Two Distinct C-H Activation Pathways Xiao Cheng, Charles Goodhue, and Jin-Quan Yu Brandeis University
I. Introduction. Peng Zhao. Liu lab
Asymmetric Total Synthesis of Mycoleptodiscin A Shupeng Zhou, Hao Chen, Yijie Luo, Wenhao Zhang and Ang Li Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai
Povarov Reaction. Zain Yousaf 10/22/2013 University of Illinois at Urbana-Champaign
Povarov Reaction Zain Yousaf 10/22/2013 University of Illinois at Urbana-Champaign Contents Introduction Chiral Lewis Acids Bronsted Acid Lanthanide complexes L-ramipril acid derived Sulfonamide Urea Derivative
Planar-Chiral Phosphine-Olefin Ligands Exploiting a (Cyclopentadienyl)manganese(I) Scaffold to Achieve High Robustness and High Enantioselectivity
Planar-Chiral Phosphine-Olefin Ligands Exploiting a (Cyclopentadienyl)manganese(I) Scaffold to Achieve High Robustness and High Enantioselectivity Reporter: Cong Liu Checker: Hong-Qiang Shen Date: 2017/02/27
Title. Author(s)Takagi, Jun; Kamon, Akihiro; Ishiyama, Tatsuo; Miyau. CitationSynlett, 2002(11): Issue Date Doc URL.
Title Synthesis of β-boryl-α,β-unsaturated Carbonyl Compou Bis(pinacolato)diboron with Vinyl Triflates Author(s)Takagi, Jun; Kamon, Akihiro; Ishiyama, Tatsuo; Miyau CitationSynlett, 2002(11): 1880-1882
Module 6 : General properties of Transition Metal Organometallic Complexes. Lecture 2 : Synthesis and Stability. Objectives
Module 6 : General properties of Transition Metal Organometallic Complexes Lecture 2 : Synthesis and Stability Objectives In this lecture you will learn the following Understand the role lead by ligands
Transition Metal-Catalyzed Carbon-Carbon Bond Cleavage (C-C Activation) Group Meeting Timothy Chang
Transition Metal-Catalyzed Carbon-Carbon Bond Cleavage (C-C Activation) Group Meeting 01-15-2008 Timothy Chang Outlines - Fundamental considerations, C-H versus C-C activation - Orbital interactions -
The Mechanism of Rhenium Catalyzed Olefination of Aldehydes. Nathan Werner Denmark Group Meeting July 22 nd, 2008
The Mechanism of Rhenium Catalyzed Olefination of Aldehydes Nathan Werner Denmark Group Meeting July 22 nd, 2008 Introduction First Use of Phosphanes to Olefinate Carbonyls: oxaphosphetane Advantages:
Literature 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,
Regioselective Reductive Cross-Coupling Reaction
Lit. Seminar. 2010. 6.16 Shinsuke Mouri (D3) Regioselective Reductive Cross-Coupling Reaction Glenn C. Micalizio obtained a Ph.D. at the University of Michigan in 2001 under the supervision of Professor
Boron containing 1,1-Dimetallicalkane Reagents
Boron containing 1,1-Dimetallicalkane Reagents Topic Talk Xun Liu July 25, 2013 Outline 1. 1,1-Borio-lithioalkane reagents 2. 1,1-Boronalkane reagents 3. 1,1-Borio-zincioalkane Reagents and 1,1-Borio-cuprioalkane
Research in our group encompasses the following 4 areas in Synthetic Organic Chemistry.
Research in our group encompasses the following 4 areas in Synthetic Organic Chemistry. 1] Development of Asymmetric Catalysis 2] Total Synthesis of Natural products 3] Development of Novel Protecting-Group-Free
Topic Review Group meeting
Topic Review Group meeting Memory of chirality Christian Gloor Based on: Zhao, H.; Hsu, D. C.; Carlier, P.R. Synthesis 2005,1, 1. Table of content > Definitions of memory of chirality > Types of chirality
First Row TM Catalyzed C-H Activation. Zhi Ren 2014/9/10
First Row TM Catalyzed C-H Activation Zhi Ren 2014/9/10 Outline 1. Introduction 2. Sc catalyzed C-H activation 3. Ti catalyzed C-H activation 4. V catalyzed C-H oxidation/fluorination 5. Mn catalyzed C-H
Domino Reactions in Total Synthesis! Reporter: Tianhe Yang! Supervisors: Prof. Yang! Prof. Chen! Prof. Tang!
1! Domino Reactions in Total Synthesis! Reporter: Tianhe Yang! Supervisors: Prof. Yang! Prof. Chen! Prof. Tang! 2! utline! 1. Brief Introduction! 2. ucleophilic Dominoes! 3. Electrophilc Dominoes! 4. Radical
Air-stable phosphine oxides as preligands for catalytic activation reactions of C Cl, C F, and C H bonds*
Pure Appl. Chem., Vol. 78, No. 2, pp. 209 214, 2006. doi:10.1351/pac200678020209 2006 IUPAC Air-stable phosphine oxides as preligands for catalytic activation reactions of C Cl, C F, and C H bonds* Lutz
Functionalization of arene and heteroarene via organic photoredox catalysis. Reporter: Fengjin Wu Supervisor: Prof. Huang Date:
Functionalization of arene and heteroarene via organic photoredox catalysis Reporter: Fengjin Wu Supervisor: Prof. Huang Date: 10. 23. 2017 Outline: 1. Background 2. Direct C-H bond functionalization of
Chiral Amplification. Literature Talk Fabian Schneider Konstanz, Universität Konstanz
Chiral Amplification Literature Talk Fabian Schneider Konstanz, 18.10.2017 Overview 1) Motivation 2) The nonlinear Effect in asymmetric catalysis - First encounters - Basic principles - Formalization and
Radical cascade reactions triggered by single electron transfer
Radical cascade reactions triggered by single electron transfer Reporter: Leming Wang Supervisor: Prof. Yong Huang 2017.11.13 Mateusz P. Plesniak, Huan-Ming Huang and David J. Procter; Nature Reviews Chemistry
Ch.16 Chemistry of Benzene: Electrophilic Aromatic Substitution
Ch.16 Chemistry of Benzene: Electrophilic Aromatic Substitution Electrophilic aromatic substitution: E + E + + Some electrophilic aromatic substitution: X N 2 S 3 R C R alogenation Nitration Sulfonation
The Chinese University of Hong Kong Department of Chemistry Research Seminar Series
Prof. Hiroyuki Nakamura Institute of Innovative Research Tokyo Institute of Technology Japan Identification and Modification of Target Proteins using Small Molecules with Light May 3, 2016 (Tuesday) 2:30