Details

Autor(en) / Beteiligte

• Yuan, Chunchen
• Zhu, Lei
• Chen, Changpeng
• Chen, Xiaolan
• Yang, Yong
• Lan, Yu
• Zhao, Yingsheng

Titel

Ruthenium(II)-enabled para-selective C-H difluoromethylation of anilides and their derivatives

Ist Teil von

• Nature communications, 2018-03, Vol.9 (1), p.1189-10, Article 1189

Ort / Verlag

England: Nature Publishing Group

Erscheinungsjahr

2018

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Transition-metal-catalyzed direct site-selective functionalization of arene C-H bonds has emerged as an innovative approach for building the core structure of pharmaceutical agents and other versatile complex compounds. However, para-selective C-H functionalization has seldom been explored, only a few examples, such as steric-hindered arenes, electron-rich arenes, and substrates with a directing group, have been reported to date. Here we describe the development of a ruthenium-enabled para-selective C-H difluoromethylation of anilides, indolines, and tetrahydroquinolines. This reaction tolerates various substituted arenes, affording para-difluoromethylation products in moderate to good yields. Results of a preliminary study of the mechanism indicate that chelation-assisted cycloruthenation might play a role in the selective activation of para-C -H bonds. Furthermore, this method provides a direct approach for the synthesis of fluorinated drug derivatives, which has important application for drug discovery and development.