Organic Letters
Organic Letters
5 years ago

Visible-Light-Triggered Directly Reductive Arylation of Carbonyl/Iminyl Derivatives through Photocatalytic PCET

Visible-Light-Triggered Directly Reductive Arylation of Carbonyl/Iminyl Derivatives through Photocatalytic PCET
Ming Chen, Wujiong Xia, Chao Yang, Xinxin Zhao
The first visible-light-mediated radical–radical cross-coupling strategy that enables the direct arylation of carbonyl/iminyl derivatives in the presence of Et3N has been realized. Such an atom-economical protocol furnishes a broad scope of arylation products such as secondary/tertiary alcohols and amines via a PCET process that facilitates the challenging reduction of C═X (X = O, N). Mechanistic investigation indicates two photocatalytic redox cycles were involved in the process, and Et3N was proved to serve as a dual reductant and proton donor. Moreover, the isolated byproducts and controlled experiments could be considered as powerful supporting evidence for our hypothesis.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01677

DOI: 10.1021/acs.orglett.7b01677

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