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26.1.4.5.2 Variation 2: With Organozinc Reagents

DOI: 10.1055/sos-SD-026-00142

Figadère, B.; Franck, X.Science of Synthesis, (200526273.

S-Ethyl thioesters react with organozinc reagents in the presence of a palladium catalyst to give ketones 49. Dichlorobis(triphenylphosphine)palladium(II) is the best catalyst for this transformation and ethylzinc iodide should be used, as diethylzinc gives the aldehyde rather than the ketone. Various organozinc reagents (e.g., alkyl, vinyl, or benzyl) as well as various thioesters (α,β-unsaturated, aromatic, bearing ketone or aldehyde groups, or derived from amino acids) can be used without side reactions such as double addition or epimerization (Scheme 46).[‌201‌]

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