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Direct Primary Amination of Alkylmetals with NH-Oxaziridine.

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.

SUBMITTER: Behnke NE

PROVIDER: S-EPMC7803087 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Direct Primary Amination of Alkylmetals with NH-Oxaziridine.

Behnke Nicole Erin NE Kielawa Russell R Kwon Doo-Hyun DH Ess Daniel H DH Kürti László L

Organic letters 20181210 24

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 ...[more]

PMID: 30525689

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