Photoinduced B-H Arylation of N-Heterocyclic Carbene Boranes with Sulfonyl(hetero)arenes

Tatsuya Nishida; Kyohei Yonekura; Katsuhiro Maeda; Eiji Shirakawa; Tsuyoshi Taniguchi

doi:10.1021/acs.orglett.4c04181

Photoinduced B-H Arylation of N-Heterocyclic Carbene Boranes with Sulfonyl(hetero)arenes

Org Lett. 2024 Dec 20;26(50):11022-11027. doi: 10.1021/acs.orglett.4c04181. Epub 2024 Dec 5.

Authors

Tatsuya Nishida¹, Kyohei Yonekura², Katsuhiro Maeda^{1

3}, Eiji Shirakawa², Tsuyoshi Taniguchi^{1

4}

Affiliations

¹ Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
² Department of Applied Chemistry for Environment, School of Biological and Environmental Sciences, Kwansei Gakuin University, Sanda, Hyogo 669-1337, Japan.
³ Nano Life Science Institute (WPI-NanoLSI), Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
⁴ Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba 305-8565, Japan.

PMID: 39638573
DOI: 10.1021/acs.orglett.4c04181

Abstract

Arylborane complexes ligated by N-heterocyclic carbenes (NHCs) can be synthesized by photoirradiation of a mixture of NHC-boranes and sulfonyl(hetero)arenes. The reaction occurs under mild and convenient conditions without any photocatalyst, which are realized by a radical chain mechanism involving NHC-boryl radicals and sulfonyl radicals. This reaction offered the opportunity to reveal the photophysical property of a 2-borylnaphtho[1,2-d]thiazole derivative.