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26.1.4.5 Method 5: Synthesis from S-Alkyl or S-Aryl Thioesters

DOI: 10.1055/sos-SD-026-00142

Figadère, B.; Franck, X.Science of Synthesis, (200526272.

Thioester derivatives are excellent candidates for acylation of organometallic species; among the most studied are S-(2-pyridyl)thioates. These thioesters react readily with organomagnesium, organocopper, and other organometallic reagents to give the corresponding ketones in high yields. The presence of a heteroatom stabilizes the tetrahedral intermediate through formation of a six-membered ring by coordination of the heteroatom [nitrogen in the case of S-(2-pyridyl)thioates] to the metal. Thus, the in situ decomposition of this intermediate is prevented and the ketone is released only during the hydrolysis step.