C3-Selective Trifluoromethylthiolation and Difluoromethylthiolation of Pyridines and Pyridine Drugs via Dihydropyridine Intermediates

• Published in: Journal of the American Chemical Society Vol. 144; no. 32; pp. 14463 - 14470
• Main Authors: Zhou, Xin-Yue, Zhang, Ming, Liu, Zhong, He, Jia-Hao, Wang, Xiao-Chen
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.08.2022; Amer Chemical Soc
• Subjects: aromatization; Chemistry; Chemistry, Multidisciplinary; drugs; Lewis acids; Lewis bases; Physical Sciences; pyridines; Science & Technology; HETEROARENES; HYDROBORATION; ACTIVATION; FUNCTIONALIZATION REACTIONS; REDUCTION; ARENES; ARYL; C-H TRIFLUOROMETHYLATION

Herein, we report a method for C3-selective C–H tri- and difluoromethylthiolation of pyridines. The method relies on borane-catalyzed pyridine hydroboration for generation of nucleophilic dihydropyridines; these intermediates react with trifluoromethylthio and difluoromethylthio electrophiles to for...