Manipulation of an electron by photoirradiation in the electron-catalyzed cross-coupling reaction.

An electron has recently been shown to catalyze the cross-coupling reaction of organometallic compounds with aryl halides. In terms of green and sustainable chemistry, the electron catalysis is much more desirable than the inevitably used transition metal catalysis but a high temperature of more than 100°C is required to achieve it. Here, we disclose that visible light photoirradiation accelerates the electron-catalyzed reaction of arylzinc reagents with aryl halides with the aid of a photoredox catalysis. Photoexcitation of a photoredox catalyst and an anion radical intermediate respectively affects the supply and transfer of the electron catalyst, promoting the cross-coupling reaction to proceed at room temperature. The supply of the electron catalyst by the photoredox catalysis makes the scope of aryl halides wider.