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