4.7 Article

Substituent-controlled site-selective silylation of 2H-indazoles to access silylated 1H-indazoles and 2H-indazoles under transition metal-free conditions

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 10, Issue 21, Pages 5389-5394

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d3qo01103h

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Herein, we describe a t-BuONa-promoted method for the site-selective silylation of 2H-indazoles. Control over the silylation site is achieved through substituents. Using SEM as a protecting group, the N-SEM 2H-indazoles can be easily deprotected and converted to silylated 1H-indazoles. This protocol shows broad substrate scope and excellent functional group tolerance, with preliminary experimental studies suggesting the involvement of silyl radicals in the reaction.
Herein, we report a t-BuONa-promoted method for the site-selective silylation of 2H-indazoles. In our system, the selective silylation of 2H-indazoles to access silylated 1H-indazoles and 2H-indazoles is controlled by substituents. Using SEM ((2-(trimethylsilyl)ethoxy)methyl) as a protecting group, N-SEM 2H-indazoles can be readily deprotected by the base and converted to silylated 1H-indazoles, thus controlling the site-selective silylation. Moreover, this protocol shows broad substrate scope and excellent functional group tolerance. Preliminary experimental studies suggest that silyl radicals are involved in the reaction.

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