Organic Dye-Catalyzed, Visible-Light Photoredox Bromination of Arenes and Heteroarenes Using -Bromosuccinimide.

Organic Dye-Catalyzed, Visible-Light Photoredox Bromination of Arenes and Heteroarenes Using -Bromosuccinimide.

Rogers, David A;Brown, Roxanne G;Brandeburg, Zachary C;Ko, Eric Y;Hopkins, Megan D;LeBlanc, Gabriel;Lamar, Angus A;
ACS omega 2018 Vol. 3 pp. 12868-12877
231
rogers2018organicacs

Abstract

A variety of arenes and heteroarenes are brominated in good to excellent yields using -bromosuccinimide (NBS) under mild and practical conditions. According to mechanistic investigations described within, the reaction is speculated to proceed via activation of NBS through a visible-light photoredox pathway utilizing erythrosine B as a photocatalyst. A photo-oxidative approach effectively amplifies the positive polarization on the bromine atom of the NBS reagent. This increase in the electrophilic nature of NBS results in drastically reduced reaction times and diversion from competing light-promoted reactive pathways.

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ID: 26441
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10.1021/acsomega.8b02320
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