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Ulm,
Pd catalysts
PdCl2(dppf)
Pd2dba3
Pd(PPh3)4
Negishi-coupling
Yong Yu, Andrew D. Bond, Philip W. Leonard, Ulrich J. Lorenz, Tatiana V. Timofeeva, K. Peter C. Vollhardt, Glenn D. Whitener and Andrey A. Yakovenko (2006). "Hexaferrocenylbenzene". Chem. Commun. (24): 2572–2574.
Negishi is better than Stille
The ZACA-ReactionZirconium-catalyzed asymmetric carboalumination
Liang, B.; Negishi, Ei-ichi. Highly Efficient Asymmetric Synthesis of Fluvirucinine A1 via Zr-Catalyzed Asymmetric Carboalumination of Alkenes (ZACA)-Lipase-Catalyzed Acetylation Tandem Process. Org. Lett. 2008, 10(2),193-195.
Motuporin-dimethyl-diester
1,3-Dienes from Alkyne and Vinyliodide
Synthesis of linear terpenes
Review: Negishi,E.; Hu, Q.; Huang, Z.; Quian, M.; Wang, G. Aldrichimica Acta 2005, 38, 71.
Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis Sambasivarao Kotha, Kakali Lahiri and Dhurke Kashinath Tetrahedron 2002, 48, 9633-9695
Suzuki-Miyaura-cross coupling
Synthesis of B2pin2
Pd[PPh3)]4
BBr3
Epothilones A (R =H= and B (R= Me)
Danishefsky, S. J. et al, Angew. Chem., Int. Ed. Eng. 1997, 36(7), 757-759
Stille CC Cross Coupling
Rate of ligand transfer (transmetalation) from tin:alkynyl > alkenyl > aryl > allyl = benzyl > α-alkoxyalkyl > alkyl
P. Espinet, A. M. Echavarren (2004). "The Mechanisms of the Stille Reaction". Angew. Chem. Int. Ed. 43 (36): 4704–4734.
Intramolecular Stille coupling
Kumada-Corriu Cross Coupling
A Kumada coupling or Kumada-Corriu coupling is a cross coupling reaction in organic chemistry between an alkyl or aryl Grignard reagent and an aryl or vinyl halocarbon catalysed by nickel or palladium. This reaction is relevant to organic synthesis because it gives access to styrene derivatives. The reaction type was reported independently by two groups in 1972, and was named after Makoto Kumada. The reaction forshadowed many related metal-catalyzed coupling reactions, such as the Sonogashira coupling and the Suzuki coupling.
Buchwald-Hartwig CN-Coupling
John P. Wolfe and Stephen L. Buchwald „Org. Synth 2004, Coll. Vol. 10: 423
Sonogashira-Castro-Reaction
Sonogashira, K.; Tohda, Y.; Hagahira, N. Tetrahedron Lett. 1975, 50, 4467
Heck Reaction
Is not a CC-coupling but olefin addition elimination process
Catalytic cycle of the Heck reaction
Stereo- and Regiochemistry
Formation of bridged rings
Bridged rings in natural products synthesis
Fused rings in natural products synthesis
Formation of spirocyclesby 6-exo-attack
Double spirocyclization
Bicyclic alkenes
Cyclizations onto acyclic alkenes
Axially chiral induction
Cascade cyclization
6-exo-cyclization
Cascade reaction
Cyclizations onto exocyclic olefins: eclipsed boat transition state
6-exo onto seven-membered ring
6-exo with stereogenic center outside the tether
7-exo cyclization
Asymmetric version
Chiral phosphines
Enantiotopos selectivity
Synthesis of polyketides
Alkaloids
Rhazinilam
Gu, Z.; Zakarian, A. Org. Lett. 2010,12, 4224-4227
References Heck-reaction(1) (a) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971,44, 581. (b) Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972,37, 2320.(2) Selected reviews include: (a) de Meijere, A.; Meyer, F. E. Angew.Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Bräse, S.; de Meijere,A. In Metal-Catalyzed Cross Coupling Reactions; Stang, P. J.,Diederick, F., Eds; Wiley-VCH: Weinheim, 1998; Chapter 3. (c)Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross CouplingReactions; Stang, P. J., Diederick, F., Eds; Wiley-VCH: Weinheim,1998; Chapter 6. (d) Link, J. T. Organic Reactions; Wiley:Hoboken, NJ, 2002; Vol. 60, Chapter 2.(3) For recent reviews of the asymmetric Heck reaction, see: (a)Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 1. (b)Donde, Y.; Overman, L. E. In Catalytic Asymmetric Synthesis;Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 8G.(4) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
Carbocyclization with Pd