Fluorodestannylation. A Powerful Technique to Liberate Anions of Oxygen, Sulfur, Selenium, and Carbon

Article abstract of DOI:10.1021/ja00231a025

Fluoride ions smoothly destannylate organotin chalcogenides to liberate nucleophilic chalcogenide ions; hence the first nucleophilic oxide (O^2-) and selenide (Se^2-) transfer agents are reported where the tin atom serves as "group 16 (VIB) transfer agent".In the presence of crown ethers or ammonium salts, this process results in a new way to generate "naked" nucleophiles.Ethers and selenides are formed in good to excellent yield.In addition, a useful C-C bond-forming reaction has been developed by using alkyltins with aldehydes and acid chlorides in the presence of fluroide ion.Aspects concerning reactivity and mechanism are presented.Finally, the generality of the fluorodestannylation procedure and the differences with parallel silicon chemistry are detailed.