Issue 1, 2023

Organophotocatalytic silyl transfer of silylboranes enabled by methanol association: a versatile strategy for C–Si bond construction

Abstract

Development of a mild, robust and metal-free catalytic approach for silyl transfer of silylboranes is critical for the advancement of modern organosilicon chemistry given their powerful capacity in the construction of C–Si bonds. Herein, we wish to disclose a visible light-induced organophotocatalytic strategy, where methanol association with boron atoms enables the photocatalytic generation of silyl radicals. Notably, the protocol is capable of accommodating a wide range of radial acceptors through slightly tuning the reaction conditions, which allows the formation of various types of C–Si bonds. The preparative power of the transformations has been further highlighted in a number of complex settings, including late-stage functionalization and radical cascade reactions. Furthermore, this technology could be extended to the construction of C–B, C–S and C–Sn bonds, thus offering a versatile platform for bond activation and connection of main group elements. The green aspect of the reaction has also been demonstrated by using Brij-30/water as a reaction solvent or sunlight as an alternative energy source.

Graphical abstract: Organophotocatalytic silyl transfer of silylboranes enabled by methanol association: a versatile strategy for C–Si bond construction

Supplementary files

Article information

Article type
Paper
Submitted
22 sept. 2022
Accepted
07 déc. 2022
First published
08 déc. 2022

Green Chem., 2023,25, 256-263

Organophotocatalytic silyl transfer of silylboranes enabled by methanol association: a versatile strategy for C–Si bond construction

Y. Wan, Y. Zhao, J. Zhu, Q. Yuan, W. Wang and Y. Zhang, Green Chem., 2023, 25, 256 DOI: 10.1039/D2GC03577D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements