Light-driven Radical-polar Crossover Catalysis Enabling Decarboxylative Fluorination of Redox Active Esters
Yunosuke Takekawa, Taiga Kodo, Kazunori Nagao, Hiroyuki Kakei, Kohei Takeuchi, Yusuke Sasaki, Hirohisa Ohmiya
Abstract
This manuscript represents an organophotoredox-catalyzed decarboxylative fluorination of alkyl redox active esters with triethylamine trihydrofluoride. The reaction proceeds through a radical-polar crossover mechanism to generate a carbocation equivalent under non-acidic and transition metal free conditions. This protocol allows delivery of various tertiary alkyl and benzyl fluorides in an environmentally benign manner. We report an organophotoredox-catalyzed decarboxylative fluorination of alkyl redox active esters with triethylamine trihydrofluoride. The reaction proceeds through a radical-polar crossover mechanism to generate a carbocation equivalent under non-acidic and transition metal free conditions. This protocol allows delivery of various tertiary alkyl and benzyl fluorides in an environmentally benign manner.