Generation of Alkyl Radical through Direct Excitation of Boracene-Based Alkylborate

Yukiya Sato; Kei Nakamura; Yuto Sumida; Daisuke Hashizume; Takamitsu Hosoya; Hirohisa Ohmiya

doi:10.1021/jacs.0c04456

Generation of Alkyl Radical through Direct Excitation of Boracene-Based Alkylborate

J Am Chem Soc. 2020 Jun 3;142(22):9938-9943. doi: 10.1021/jacs.0c04456. Epub 2020 May 18.

Authors

Yukiya Sato¹, Kei Nakamura¹, Yuto Sumida^{1

2}, Daisuke Hashizume³, Takamitsu Hosoya^{2

4}, Hirohisa Ohmiya^{1

5}

Affiliations

¹ Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
² Laboratory for Chemical Biology, RIKEN Center for Biosystems Dynamics Research (BDR), 6-7-3 minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan.
³ RIKEN Center for Emergent Matter Science (CEMS), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
⁴ Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
⁵ JST, PRESTO, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.

PMID: 32396733
DOI: 10.1021/jacs.0c04456

Abstract

The generation of tertiary, secondary, and primary alkyl radicals has been achieved by the direct visible-light excitation of a boracene-based alkylborate. This system is based on the photophysical properties of the organoboron molecule. The protocol is applicable to decyanoalkylation, Giese addition, and nickel-catalyzed carbon-carbon bond formations such as alkyl-aryl cross-coupling or vicinal alkylarylation of alkenes, enabling the introduction of various C(sp³) fragments to organic molecules.

Publication types

Research Support, Non-U.S. Gov't