Science of Synthesis

Chartoire, A.; Nolan, S. P., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013) 1, 523.

Acylsilanes ‌39‌ can be coupled with various organic halides in the presence of copper, and in some cases palladium, to yield the corresponding enol silyl ethers ‌40‌/‌41‌ (‌Scheme 10‌).[‌39‌] The first step involves the generation of an alkenylcopper species by 1,2-C(sp2)-to-O silyl migration of the acylsilane using tert-butoxycopper(I) in dimethylformamide. The cross coupling is then achieved by adding a halide. If the halide is allylic, benzylic, or an alkyl derivative, the reaction does not require palladium to form products ‌40‌. On the other hand, if the halide is an aryl or a vinyl derivative, then the reaction requires the use of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) for the formation of products ‌41‌.

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