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Issue 43, 2020
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β-Silicon-effect-promoted intermolecular site-selective C(sp3)–H amination with dirhodium nitrenes

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Abstract

A dirhodium-catalyzed, β-selective C–H amination of organosilicon compounds has been developed. Primary C(sp3)–H bonds of silylethyl groups and secondary C(sp3)–H bonds of silacycloalkanes can be selectively converted to C–N bonds at the β-position of the silicon atoms. The experimental data and theoretical calculations indicate that the strong σ-donor ability of the carbon–silicon bonds is responsible for the β-selectivity. Kinetic isotope effects clearly demonstrate that the C–H bond cleavage step is not turnover-limiting, but selectivity-determining.

Graphical abstract: β-Silicon-effect-promoted intermolecular site-selective C(sp3)–H amination with dirhodium nitrenes

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Supplementary files

Article information


Submitted
06 Feb 2020
Accepted
15 Apr 2020
First published
16 Apr 2020

Chem. Commun., 2020,56, 5759-5762
Article type
Communication

β-Silicon-effect-promoted intermolecular site-selective C(sp3)–H amination with dirhodium nitrenes

R. Ninomiya, K. Arai, G. Chen, K. Morisaki, T. Kawabata and Y. Ueda, Chem. Commun., 2020, 56, 5759
DOI: 10.1039/D0CC00959H

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