Issue 41, 2024

Grignard reagents as simple precatalysts for the dehydrocoupling of amines and silanes

Abstract

Methyl magnesium bromide is a precatalyst for the dehydrocoupling of silanes and amines to produce aminosilane products under mild conditions. As a commercially available Grignard reagent, this precatalyst represents a simplification over previous magnesium-containing catalysts for Si–N bond formation while displaying similar activity to other magnesium-based catalysts. This observation is consistent with the hypothesis that competitive Schlenk equilibrium can be addressed by not using an ancillary ligand. While the activity of MeMgBr is lower than some reported catalysts, including other commercially available precatalysts, unique selectivity was observed for MeMgBr that may allow for directed synthesis of aminosilane products. This work continues to increase the accessibility of Si–N heterodehydrocoupling through a growing family of commercially available precatalysts that balance activity and selectivity.

Graphical abstract: Grignard reagents as simple precatalysts for the dehydrocoupling of amines and silanes

Supplementary files

Article information

Article type
Paper
Submitted
23 Aug 2024
Accepted
10 Sep 2024
First published
18 Sep 2024

Dalton Trans., 2024,53, 16843-16848

Grignard reagents as simple precatalysts for the dehydrocoupling of amines and silanes

C. E. Bushey, D. R. Javier-Jiménez, M. B. Reuter and R. Waterman, Dalton Trans., 2024, 53, 16843 DOI: 10.1039/D4DT02403F

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