Alkyne Dicobalt Complexes in Organic Chemistry
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1 Alkyne Dicobalt Complexes in Organic Chemistry Sun Baochuan Supervisors: Prof. Yang Prof. Chen Prof. Tang
2 Cobalt - Co From German word kobald - evil spirits Atomic Number: 27 Group: 9 Period: 4 3d 7 4s 2 Oxidative State: I, II, III Vitamin B 12 Dyes Super Alloys 1
3 Three characteristic reactions of cobalt Characteristic property of cobalt 1. High affinity to C C or C N unsaturated π- bonds 2. High affinity to carbonyl group. 3. Easy to form a square planar bipyramidal six - coordination with four nitrogen atoms or two nitrogen atoms and two oxygen atoms. Reaction type Reactions with unsaturated π- bond Reactions with carbonyl groups Reactions with vitamin B 12 type compounds. Reaction 1. Reactions with a Co 2 (CO) 6 protection group 2. Nicholas reactions 3. Pauson Khand reations 4. [ ] cyclotrimerizations and other cyclizations. 1. Hydroformylations 2. Hydrocarbonylations 3. Amidocarbonylations 4. Hydrosilylcarbonylations 5. Carbonylations of halides 6. Other carbonylations 1. Diels -Alder reactions 2. Cyclopropanations 3. Carbonyl ene reactions 4. Henry reactions 5. Boron hydride reductions, etc. Omae, I. Appl. Organometal. Chem. 2007, 21,
4 Alkyne - dicobalt complexes Typically dark and red liquids or solids Easy to purify by crystallization or chromatography Can be stored in air for long periods of time. Release alkyne Ce(IV) Fe(III) Amine N-oxides Advances in organiometallic chemistry. Volume 41; Stone, F. G., West, R., Eds.; Academic Press: San Diego,
5 4 Alkyne - dicobalt complexes Pauson-Khand reaction Nicholas reaction Protecting group
6 5 Pauson-Khand reaction Formal [2+2+1} cyclization High selectivity for alkyne: R 2 >R 1 Low yield Harsh conditions for alkenes except strained olefins and ethylene Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin. Trans , 977. Mechanism Stereoselectivity Reactivity Catalytic version
7 Pauson-Khand reaction - Mechanism Magnus, P.; Exon, C.; Robertson, P. A. Tetrahedron. 1985, 41,
8 7 Pauson-Khand reaction - Mechanism Yamanaka, M.; Nakamura, E. J. Am. Chem. Soc. 2001, 123, 1703
9 Pauson-Khand reaction - Mechanism Pericas, M. A.; Balsells, J.; Castro, J.; Marchueta, I.; Riera, A.; Vazquez, J.; Verdaguer, X. Pure Appl. Chem. 2002, 74,
10 Pauson-Khand reaction - Mechanism Banide, E. V.; Muller Bunz, H.; Manning, A. R.; Evans, P.; McGlinchey, M. J. Angew, Chem, Int, Ed. 2007, 46,
11 10 Pauson-Khand reaction - Mechanism Pallerla, M. K.; Yap, G. P. A.; Fox, J. M. J. Org. Chem. 2008, 73, 6137.
12 Pauson-Khand reaction - Reactivity Intramolecular: Traceless tether: Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436 Reichwein, J. F.; Iacono, S. F.; Pagenkopf, B. L. Tetrahedron. 2002, 58,
13 Pauson-Khand reaction - Reactivity N-oxide: Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289 Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115,
14 13 Pauson-Khand reaction - Reactivity Lewis base: Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew, Chem, Int, Ed, Engl. 1997, 36, 24. Sugihara, T.; Yamada, M.; Yamaguchi, M.; Nishizawa, M. Synlett, 1999, 6, 771. Perez del Valle, C.; Milet, A.; Gimbert, Y.; Greene, A. E. Angew. Chem. Int. Ed
15 Pauson-Khand reaction - Reactivity DSAC: dry state adsorption conditions Microwave: Smit, W. A.; Gybin, A. S.; Shashkov, A. S. Tetrahedron Lett. 1986, 27, Fisher, S.; Groth, U.; Jung, M.; Schneider, A. Synlett, 2002, 12,
16 Pauson-Khand reaction - Reactivity Alkene Reactivity : cyclohexene < cyclopentene < norbornene ( 降冰片烯 ) De Bruin, T. J. M.; Milet, A.; Greene, A. E.; Gimbert, Y.; J. Org. Chem. 2004, 69,
17 16 Pauson-Khand reaction - Stereoselctivity Approaches: Chiral precursors Chiral promoters Chiral auxiliaries Chiral ligand Chiral auxiliaries: Fonquerna, S.; Moyano, A.; Pericas, M. A.; Riera, A. J. Am. Chem. Soc. 1997, 119,
18 Pauson-Khand reaction - Stereoselctivity Chiral promoters: Chiral ligand: Kerr, W. J.; Kirk, G. G.; Middlemiss, D. Synlett, 1995, 10, Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. J. Am. Chem. Soc. 2000, 122,
19 Pauson-Khand reaction - catalytic A straightforward solution: Laschat, S.; Becheanu, A.; Bell, T.; Baro, A. Synlett, 2005, 17, Additives: Bu 3 PS, CyNH 2, etc. 18
20 Pauson-Khand reaction - catalytic Catalytic with other Co source: Cat:(indenyl)Co(COD) Lee, B. Y.; Chuang, Y. K. J. Am. Chem. Soc. 1994, 116, Lee, N. Y.; Chuang, Y. K. Tetrahedron Lett. 1996, 37,
21 20 Pauson-Khand reaction - catalytic Yuefan, W; Lingmin, X; Ruocheng, Y.; Jiahua, C.; Zhen, Y. Chem. Commun. 2012, 48, 8183.
22 Nicholas reaction Stable in dry air, stored indefinitely under N 2 Positive charge highly delocalized Comparable stability with Ar 3 C + Varghese, V.; Saha, M.; Nicholas, K. M. Org. Synth. 1989, 67, 141. Nicholas, K. M.; Acc. Chem. Res. 1987, 20,
23 Nicholas reaction Synthesis of propargylic carbocation: Teobald, B. J.; Tetrahedron. 2002, 58,
24 Nicholas reaction Synthesis propargylic carbocation: Teobald, B. J.; Tetrahedron. 2002, 58,
25 Nicholas reaction React with nucleophiles: Teobald, B. J.; Tetrahedron. 2002, 58,
26 Nicholas reaction React with nucleophiles: Other Nucleophiles: H - :NaBH 4 N:amines S F - etc. Advantage: Teobald, B. J.; Tetrahedron. 2002, 58, Muller, T. J. J. Eur. J. Org. Chem. 2001, 11,
27 Protecting group Protection: Co 2 (CO) 8 CoBr 2, Zn, CO Deprotection: Fe(III) Ce(IV) Amine N-oxides Advances in organometallic chemistry. Volume 41; Stone, F. G., West, R., Eds.; Academic Press: San Diego, 1997 BH 3 - H 2 O 2 /OH - EtMgCl NaBH 4 Metathesis CH 3 COCl AlCl 3 Teobald, B. J.; Tetrahedron. 2002, 58, etc. 26
28 27 Summary Mechanism (decarbonylation / alkene insertion) PKR Reactivity ( additives / modified methods) Stereoselectivity Catalytic Nicholas Reaction Protecting group
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