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Direct Primary Amination of Alkylmetals with NH-Oxaziridine

Nicole Erin Behnke, Russell Kielawa, Doo-Hyun Kwon, Daniel H. Ess, László Kürti*

*Department of Chemistry, Rice University BioScience Research Collaborative, 6500 Main Street, Rm 380, Houston, Texas 77030, United States, Email: kurti.laszlorice.edu

N. E. Behnke, R. Kielawa, D.-H. Kwon, D. H. Ess, L. Kürti, Org. Lett., 2018, 20, 8064-8068.

DOI: 10.1021/acs.orglett.8b03734 (free Supporting Information)



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Abstract

A bench-stable NH-oxaziridine reagent enables a primary electrophilic amination of primary, secondary, and tertiary organometallic substrates. This facile and highly chemoselective transformation occurs in a single step without transition metal catalysts at ambient temperature. A convenient extractive work-up provides alkylamine products.

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Key Words

primary amines


ID: J54-Y2018