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Direct Primary Amination of Alkylmetals with NH-Oxaziridine. | LitMetric

Direct Primary Amination of Alkylmetals with NH-Oxaziridine.

Org Lett

Department of Chemistry , Rice University BioScience Research Collaborative, 6500 Main Street , Rm 380, Houston , Texas 77030 , United States.

Published: December 2018

AI Article Synopsis

Article Abstract

A method for the primary electrophilic amination of primary, secondary, and tertiary organometallic substrates from a bench-stable NH-oxaziridine reagent is described. This facile and highly chemoselective transformation occurs at ambient temperature and without transition metal catalysts or purification by column chromatography to provide alkylamine products in a single step. Density functional theory (DFT) calculations revealed that, despite the basicity of alkylmetals, the direct NH-transfer pathway is favored over proton and O-transfer.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7803087PMC
http://dx.doi.org/10.1021/acs.orglett.8b03734DOI Listing

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