Commercially available organolithium compounds as effective, simple precatalysts for silicon-nitrogen heterodehydrocoupling

A family of commercially available organolithium compounds were found to effectively catalyze the heterodehydrocoupling of silanes and amines under ambient conditions. Ubiquitous n BuLi ( 1 ) was utilized as the benchmark catalyst, where an array of primary, secondary, and tertiary arylsilanes were...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2023-10, Vol.52 (38), p.13497-1356
Main Authors: Reuter, Matthew B, Bushey, Claire E, Javier-Jiménez, Diego R, Waterman, Rory
Format: Article
Language:English
Subjects:
Amines
Organolithium compounds
Reagents
Silicon
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Summary:A family of commercially available organolithium compounds were found to effectively catalyze the heterodehydrocoupling of silanes and amines under ambient conditions. Ubiquitous n BuLi ( 1 ) was utilized as the benchmark catalyst, where an array of primary, secondary, and tertiary arylsilanes were coupled to electron-donating amines, affording aminosilanes in high conversions with short reaction times. Preliminary mechanistic analysis is consistent with a nucleophilic-type system that involves the formation of a hypervalent silicon intermediate. This work underscores the accessibility of Si-N heterodehydrocoupling, with organolithium reagents emerging as some of the most straightforward and cost-effective precatalysts for this transformation. A family of commercially available organolithium compounds were found to effectively catalyze the heterodehydrocoupling of silanes and amines under ambient conditions.
ISSN:1477-9226
1477-9234
DOI:10.1039/d3dt02564k