Visible-Light-Driven Silyl or Germyl Radical Generation via Si-C or Ge-C Bond Homolysis

Bi-Xiao Li; Hiroshi Ishida; Chao Wang; Masanobu Uchiyama

doi:10.1021/acs.orglett.3c00503

Visible-Light-Driven Silyl or Germyl Radical Generation via Si-C or Ge-C Bond Homolysis

Org Lett. 2023 Mar 17;25(10):1765-1770. doi: 10.1021/acs.orglett.3c00503. Epub 2023 Mar 8.

Authors

Bi-Xiao Li¹, Hiroshi Ishida¹, Chao Wang¹, Masanobu Uchiyama^{1

2}

Affiliations

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
² Research Initiative for Supra-Materials, Shinshu University, 4-17-1 Wakasato, Nagano-shi, Nagano 380-8553, Japan.

PMID: 36883960
DOI: 10.1021/acs.orglett.3c00503

Abstract

We report a simple, rapid, and selective protocol for visible-light-driven generation of silyl radicals through photoredox-induced Si-C bond homolysis. Irradiating 3-silyl-1,4-cyclohexadienes with blue light in the presence of a commercially available photocatalyst smoothly generated silyl radicals bearing various substituents within 1 h, and these radicals were trapped by a broad range of alkenes to afford products in good yields. This process is also available for efficient generation of germyl radicals.