Issue 8, 2024

Photo-induced catalyst-free formal carbon insertion of acylsilanes into B–B and B–Si bonds

Abstract

A formal carbon insertion of acylsilanes into B–B and B–Si bonds has been developed. The in situ formed siloxycarbene from acylsilane under blue LED irradiation worked as the intermediate for the reaction. Commercially available B2(pin)2 and (pin)B-SiMe2Ph were employed as cross partners. No base or catalyst was needed. Both aromatic acylsilanes and aliphatic acylsilanes were applicable. The yields were up to 99% and the utility of the product was demonstrated. When 2-furyl and 2-thiophenyl acylsilanes were used, the B(pin) ring was enlarged to a six-membered ring through the siloxy group rearrangement from carbon to boron.

Graphical abstract: Photo-induced catalyst-free formal carbon insertion of acylsilanes into B–B and B–Si bonds

Supplementary files

Article information

Article type
Research Article
Submitted
23 Jan 2024
Accepted
22 Feb 2024
First published
22 Feb 2024

Org. Chem. Front., 2024,11, 2339-2343

Photo-induced catalyst-free formal carbon insertion of acylsilanes into B–B and B–Si bonds

X. Lu, Q. Zhao, H. Zhang, P. Xu, X. Chen and Z. Liu, Org. Chem. Front., 2024, 11, 2339 DOI: 10.1039/D4QO00139G

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