Chemoselective Synthesis of 3-Bromomethyloxindoles via Visible-Light-Induced Radical Cascade Bromocyclization of Alkenes
Ming‐Zhong Zhang, Xin Yang, Jin-Xing Yin, Ya Deng, Hong-Ying Tan, Yu‐Heng Bai, Yalin Li, Jiangwei Wen, Tieqiao Chen
Abstract
A novel visible-light-induced radical cascade bromocyclization of N -arylacrylamides has been accomplished. This reaction overcomes the overbromination at the benzene rings suffered in traditional electrophilic reactions, thus enabling the first highly chemoselective synthesis of valuable 3-bromomethyloxindoles. The combination of pyridine and anhydrous medium is identified as the key factor for the high chemoselectivity in the current photoreaction system, which might work by suppressing the in situ generation of low-concentration Br 2 from N -bromosuccinimide. Moreover, the mild reaction conditions ensure the generation of a wide range of the new desired products with excellent functional group tolerance.