And the Stille reaction

Palladium-catalyzed carbon-carbon bond forming reactions like the Suzuki reac-tion as well as the Heck reaction and the Stille reaction, have in recent years gained increased importance in synthetic organic chemistry. In case of the Suzuki reaction, an organoboron compound—usually a boronic acid—is reacted with an aryl (or alkenyl, or alkynyl) halide in the presence of a palladium catalyst. 

Many types of functional groups are tolerated in a Suzuki reaction, and the yields are often good to very good. The presence of a base, e.g. sodium hydroxide or sodium/potassium carbonate, is essential for this reaction. The base is likely to be involved in more than one step of the catalytic cycle, at least in the transmetal-lation step. Proper choice of the base is important in order to obtain good results." In contrast to the Heck reaction and the Stille reaction, the Suzuki reaction does not work under neutral conditions. 

R. Franzen, The Suzuki, the Heck, and the Stille Reaction Three Versatile Methods for the Introduction of New C-C Bonds on Solid Support, Can. J. Chem. 2000, 78, 957-962. 

Baumgartner, M.T., Tempesti, T.C. and Pierini, A.B. (2003) Steric effects in the synthesis of ortho-substituted 1,1 -binaphthalene derivatives by the SRN1 and the Stille reaction. ARKIVOK, X, 420 133. 

Further typical reactions of imidoylstannanes are shown in Scheme 6-5.71 Butyl-lithium reacts to form the imidoyllithium, which reacts with electrophiles such as alkyl halides, silyl chlorides, aldehydes, or chloroformates,75 and the Stille reaction with an acyl halide gives an a-carbonylimide which can be hydrolysed to an a-dicarbonyl compound.75... 

The same authors reported the superior activity of PdCl2 dissolved in 95, in both the Heck and the Stille reaction. ... 

Transition-metal-mediated transformations play an important role in combinatorial synthesis on solid supports because they allow C-C bond formation under mild, neutral conditions and tolerate a broad range of functional groups. In particular, the palladium-mediated cross-coupling reactions, more precisely the Mizoroki-Heck, the Suzuki and the Stille reactions received a lot of attention due to their enormous derivatization potential of functional structures [5]. Although Stille coupling was the first to be explored on and... 

Nader, M. W., Oberdorfer, F. 2002. Syntheses of [carbonyl-C-ll]2-(2-benzoylphenoxy)-AJ-phenylacet-amide from [C-ll]carbon monoxide by the Suzuki and the Stille reactions. Appl. Radial. Isol 57 681-685. 

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