期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 61, 期 36, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202208089
关键词
Benzamide Derivatives; Iminium Activation; Para-Selectivity; Photoredox Catalysis; Trifluoromethylation
资金
- National Natural Science Foundation of China [21971267]
- Fundamental Research Funds for the Central Universities, Sun Yat-sen University [22lgqb34]
- program for Guangdong Introducing Innovative and Entre-preneurial Teams [2017ZT07C069]
The direct C-H trifluoromethylation of arenes via a radical pathway has recently gained considerable attention. However, a major challenge in C-H trifluoromethylation is the lack of site-selectivity on the phenyl ring, especially para-selectivity. Here, we demonstrate a new strategy for para-selective C-H trifluoromethylation of benzamide derivatives using iminium activation.
The direct C-H trifluoromethylation of arenes via a radical pathway has attracted considerable attention recently. However, a major challenge of C-H trifluoromethylation is the lack of site-selectivity on the phenyl ring especially para-selectivity. Herein we show a new strategy for para-selective C-H trifluoromethylation of benzamide derivatives using iminium activation. The reaction undergoes a radical-type nucleophilic substitution instead of a radical-type electrophilic substitution owing to iminium activation as a result of lowering the LUMO (lowest unoccupied molecular orbital). A wide range of substrates are compatible with this method giving almost exclusive para-trifluoromethylated products.
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