Metal-Free Amino(hetero)arylation and Aminosulfonylation of Alkenes Enabled by Photoinduced Energy Transfer

• Published in: Journal of the American Chemical Society Vol. 145; no. 30; pp. 16630 - 16641
• Main Authors: Qi, Xu-Kuan, Zheng, Meng-Jie, Yang, Chao, Zhao, Yating, Guo, Lin, Xia, Wujiong
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 02.08.2023; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; DIFUNCTIONALIZATION; FUNCTIONALIZATION; ROOM-TEMPERATURE; AMINOARYLATION; ARYL DIAZONIUM SALTS; C-H ARYLATION; PHOTOREDOX; AMINOALKYL RADICALS; CARBOAMINATION; ARYLSULFONYL CHLORIDES
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/jacs.3c04073

β-(Hetero)­arylethylamines are privileged structural motifs found in many high-value organic molecules, including pharmaceuticals and natural products. To construct these important molecular skeletons, previous methods are mainly achieved by amino­(hetero)­arylation reaction with the aid of transition metals and preactivated substrates. Herein, we report a metal-free and photoinduced intermolecular amino­(hetero)­arylation reaction for the single-step installation of both (hetero)­aryl and iminyl groups across alkenes in an efficient and regioselective manner. This method shows broad scope (up to 124 examples) and excellent tolerance of various olefinsfrom the simplest ethylene to complex multisubstituted alkenes can all participate in the reaction. Furthermore, aminosulfonylation of alkenes can be also conducted in the presence of sodium bisulfite as the SO2 source.