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Photoredox‐Catalyst‐Enabled para ‐Selective Trifluoromethylation of tert ‐Butyl Arylcarbamates
Author(s) -
Jiang Yaqiqi,
Li Bao,
Ma Nana,
Shu Sai,
Chen Yujie,
Yang Shan,
Huang Zhibin,
Shi Daqing,
Zhao Yingsheng
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202105631
Subject(s) - trifluoromethylation , reagent , chemistry , trifluoromethyl , catalysis , photoredox catalysis , combinatorial chemistry , ring (chemistry) , photocatalysis , organic chemistry , photochemistry , alkyl
The direct incorporation of a trifluoromethyl group on an aromatic ring using a radical pathway has been extensively investigated. However, the direct highly para ‐selective C−H trifluoromethylation of a class of arenes has not been achieved. In this study, we report a light‐promoted 4,5‐dichlorofluorescein (DCFS)‐enabled para ‐selective C−H trifluoromethylation of arylcarbamates using Langlois reagent. The preliminary mechanistic study revealed that the activated organic photocatalyst coordinated with the arylcarbamate led to para ‐selective C−H trifluoromethylation. Ten‐gram scale reaction performs well highlighting the synthetic importance of this new protocol.