Issue 66, 2022

Intramolecular activation of strong Si–O bonds by gold(i): regioselective synthesis of 3-bromo-2-silylbenzofurans

Abstract

The high reactivity of gold-vinylidene complexes, generated in situ by [1,2]-bromine shift from the corresponding 1-bromoalkynes, allows the activation of one of the strongest bonds in organic chemistry (Si–O), strategically placed at the ortho-position. In this way, the synthesis of 3-bromo-2-silylbenzofuranes is achieved in good yields. Several substituents with different electronic properties and substitution patterns are well tolerated on the tethering aromatic ring as well as a number of silyl groups on the O-atom. A preliminary mechanistic study is compatible with the participation of gold vinylidene intermediate species. The synthetic applicability of the obtained scaffolds was preliminarily showcased by orthogonal C–C bond forming transformations.

Graphical abstract: Intramolecular activation of strong Si–O bonds by gold(i): regioselective synthesis of 3-bromo-2-silylbenzofurans

Supplementary files

Article information

Article type
Communication
Submitted
31 Mud 2022
Accepted
19 Maw 2022
First published
20 Maw 2022

Chem. Commun., 2022,58, 9250-9253

Intramolecular activation of strong Si–O bonds by gold(I): regioselective synthesis of 3-bromo-2-silylbenzofurans

P. Fernández-Canelas, R. Miguélez, E. Rubio, J. M. González and P. Barrio, Chem. Commun., 2022, 58, 9250 DOI: 10.1039/D2CC03060H

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