Photoinduced 1,2-dicarbofunctionalization of alkenes with organotrifluoroborate nucleophiles<i>via</i>radical/polar crossover
María Jesús Cabrera‐Afonso, Anasheh Sookezian, Shorouk O. Badir, Mirna El Khatib, Gary A. Molander
Abstract
-(acyloxy)phthalimide redox-active esters as radical progenitors and organotrifluoroborates as carbon-centered nucleophiles is reported. This redox-neutral, multicomponent reaction is postulated to proceed through photochemical radical/polar crossover to afford a key carbocation species that undergoes subsequent trapping with organoboron nucleophiles to accomplish the carboallylation, carboalkenylation, carboalkynylation, and carboarylation of alkenes with regio- and chemoselective control. The mechanistic intricacies of this difunctionalization were elucidated through Stern-Volmer quenching studies, photochemical quantum yield measurements, and trapping experiments of radical and ionic intermediates.