Affiliation:
1. Department of Chemistry Zhejiang University 310058 Hangzhou People's Republic of China
Abstract
AbstractDearomative trifluoromethylation of arenes provides an ideal method for constructing CF3‐containing three‐dimensional architectures which are of increasing interest in drug discovery. However, such transformation is rare and challenging because of the inherently low reactivity of arene π‐systems and selectivity issues. Herein, we disclose a general dearomative 1,2‐hydrotrifluoromethylation of (hetero)arenes utilizing activation by temporary π‐complexation to chromium, thus affording convenient access to 1,3‐cyclohexadienes bearing the privileged CF3 group. The versatility of this strategy further enables a dearomative 1,2‐deuterotrifluoromethylation with high deuterated ratios. The related dearomative 1,2‐(deutero)hydroperfluoroethylation reactions were conducted well for a range of chromium‐bound (hetero)arenes. Finally, a reasonable mechanism was proposed based on the intermediate capture and control experiments.
Funder
National Natural Science Foundation of China
Fundamental Research Funds for the Central Universities