Base-induced azofluoroalkylation of unactivated alkenes via halogen atom transfer

Abstract

The practical and efficient incorporation of fluoroalkyl moieties from commercially available fluoroalkyl halides into molecules is appealing but still challenging. Herein, we disclose a base-induced three-component coupling employing unactivated alkenes, fluoroalkyl iodides and diazonium salts. A thermally and kinetically favored halogen atom transfer (XAT) process between the fluoroalkyl iodides and aryl radicals originally from diazonium salts affords fluoroalkyl radicals promoting the addition to alkene and subsequent diazene trapping. This protocol offers a new approach for facile and precise synthesis of a wide range of β-perfluorinated amine surrogates under transition-metal-free conditions. The synthetic utility of the method is demonstrated by Fischer-type synthesis of fluorinated indoles and dihydropyridazinones and their potential antifungal activity studies.