Organic Letters
Organic Letters
5 years ago

Selective Aerobic C–H Amination of Phenols with Primary Amines over Copper toward Benzoxazoles

Selective Aerobic C–H Amination of Phenols with Primary Amines over Copper toward Benzoxazoles
Shaofeng Wu, Shuang-Feng Yin, Liang-Wei Qian, Yongbo Zhou, Long Liu, Jianyu Dong, Qing Xu
Using O2 as the oxidant, the benzoxazole frameworks can be directly constructed from the readily available phenols and primary amines in the presence of NH4PF6 over copper under mild conditions. Mechanistic studies showed that a novel mechanism involving biphenyldiols and o-quinones very possibly takes effect in the reaction, because both can selectively give the benzoxazoles under the reaction conditions. An unprecedented unstrained Caryl–Caryl bond cleavage takes place in the reaction.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01061

DOI: 10.1021/acs.orglett.7b01061

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