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

Chunchen Yuan, Lei Zhu, Changpeng Chen, Xiaolan Chen, Yong Yang, Yu Lan () and Yingsheng Zhao ()
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Chunchen Yuan: Chemical Engineering, and Materials Science Soochow University
Lei Zhu: School of Chemistry and Chemical Engineering Chongqing University
Changpeng Chen: Chemical Engineering, and Materials Science Soochow University
Xiaolan Chen: Chemical Engineering, and Materials Science Soochow University
Yong Yang: Chinese Academy of Science
Yu Lan: School of Chemistry and Chemical Engineering Chongqing University
Yingsheng Zhao: Chemical Engineering, and Materials Science Soochow University

Nature Communications, 2018, vol. 9, issue 1, 1-10

Abstract: Abstract 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-CAr–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.

Date: 2018
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DOI: 10.1038/s41467-018-03341-6

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