Direct oxygen insertion into C-C bond of styrenes with air

Qixue Qin (), Liang Zhang, Jialiang Wei, Xu Qiu, Shuanghong Hao, Xiao- De An and Ning Jiao ()
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Qixue Qin: Chang Cheng Rd. 700
Liang Zhang: Chang Cheng Rd. 700
Jialiang Wei: Peking University
Xu Qiu: Peking University
Shuanghong Hao: Chang Cheng Rd. 700
Xiao- De An: Chang Cheng Rd. 700
Ning Jiao: Peking University

Nature Communications, 2024, vol. 15, issue 1, 1-7

Abstract: Abstract Skeletal editing of single-atom insertion to basic chemicals has been demonstrated as an efficient strategy for the discovery of structurally diversified compounds. Previous endeavors in skeletal editing have successfully facilitated the insertion of boron, nitrogen, and carbon atoms. Given the prevalence of oxygen atoms in biologically active molecules, the direct oxygenation of C-C bonds through single-oxygen-atom insertion like Baeyer-Villiger reaction is of particular significance. Herein, we present an approach for the skeletal modification of styrenes using O2 via oxygen insertion, resulting in the formation of aryl ether frameworks under mild reaction conditions. The broad functional-group tolerance and the excellent chemo- and regioselectivity are demonstrated in this protocol. A preliminary mechanistic study indicates the potential involvement of 1,2-aryl radical migration in this reaction.

Date: 2024
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DOI: 10.1038/s41467-024-53266-6

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