Visible-Light-Promoted Photocatalytic B-C Coupling via a Boron-Centered Carboranyl Radical: Facile Synthesis of B(3)-Arylated o-Carboranes

Angewandte Chemie
Da Zhao, Zuowei Xie

Abstract

A visible-light-mediated in situ generation of a boron-centered carboranyl radical (o-C2 B10 H11(.)) has been described. With eosin Y as a photoredox catalyst, 3-diazonium-o-carborane tetrafluoroborate [3-N2-o-C2B10H11][BF4] was converted into the corresponding boron-centered carboranyl radical intermediate, which can undergo efficient electrophilic substitution reaction with a wide range of (hetero)arenes. This general and simple procedure provides a metal-free alternative for the synthesis of 3-(hetero)arylated-o-carboranes.

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Citations

Feb 23, 2017·The Journal of Organic Chemistry·Chao WuDongmei Lu
Feb 23, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Ahmet Nedim AyBirgul Zumreoglu-Karan
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Jan 5, 2019·Chemical Society Reviews·François-Xavier Felpin, Saumitra Sengupta
Apr 16, 2019·Angewandte Chemie·Peng-Fei CuiGuo-Xin Jin
Mar 16, 2021·Journal of the American Chemical Society·Yik Ki AuZuowei Xie
Feb 20, 2020·Journal of the American Chemical Society·Harrison A MillsAlexander M Spokoyny
Dec 10, 2016·Journal of the American Chemical Society·Jonathan C AxtellAlexander M Spokoyny

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