Successive C–C bond cleavage, fluorination, trifluoromethylthio- and pentafluorophenylthiolation under metal-free conditions to provide compounds with dual fluoro-functionalization?

Chemical Science Pub Date: 2015-12-09 DOI: 10.1039/C5SC04208A

Abstract

The selective C–C bond cleavage and simultaneous formation of two C–F bonds and one C–S bond in β-keto esters with nucleophilic fluorination reagents such as DAST under metal-free/catalyst-free conditions is disclosed. Double fluorination at two remote carbons with additional dialkylamino-sulfenylation provided unique fluorinated compounds in good to high yields. This method can be applied for the successive C–C bond cleavage/fluorination/trifluoromethylthiolation of β-keto esters using trifluoromethyl-DAST (CF3-DAST) providing different type of fluorinated and trifluoromethylthiolated compounds via a shunt pathway. Doubly fluoro-functionalized compounds obtained in these reactions are unique and difficult to synthesize by other methods.

Graphical abstract: Successive C–C bond cleavage, fluorination, trifluoromethylthio- and pentafluorophenylthiolation under metal-free conditions to provide compounds with dual fluoro-functionalization
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