Decarbethoxylative Arylation Employing Arynes: A Metal-Free Pathway to Arylfluoroamides.

Abstract

An efficient, metal-free decarbethoxylative arylation protocol for the synthesis of α-aryl-α-fluoroamides from fluoromalonamates, under ambient reaction conditions using aryne as an electrophilic arylating agent, is reported. This decarbethoxylative arylation proceeds under mild conditions and provides a practical and effective entry to a wide range of α-aryl-α-fluoroacetamides. Interestingly, the use of the tert-butyl ester of fluoromalonamate prevented the otherwise rapid decarboxylation step, affording the arylated fluoromalonamate in moderate yield.