Issue 5, 2018

Radical-mediated intramolecular β-C(sp3)–H amidation of alkylimidates: facile synthesis of 1,2-amino alcohols

Abstract

A new radical-mediated intramolecular β-C(sp3)–H amidation reaction of O-alkyl trichloro- or arylimidates is reported. Various oxazolines were efficiently prepared from easily accessible alcohol starting materials. The trichloro-oxazoline products can be hydrolyzed under mild conditions to give valuable 1,2-amino alcohols. This amidation reaction exhibits a broad substrate scope and good functional group tolerance, and offers a powerful means for the C(sp3)–H functionalization of alcohols. Mechanistic studies suggest that a sequence of 1,5-HAT of an imidate radical, iodination and cyclization might be operative.

Graphical abstract: Radical-mediated intramolecular β-C(sp3)–H amidation of alkylimidates: facile synthesis of 1,2-amino alcohols

Supplementary files

Article information

Article type
Communication
Submitted
21 Nov. 2017
Accepted
13 Dec. 2017
First published
13 Dec. 2017

Chem. Commun., 2018,54, 515-518

Radical-mediated intramolecular β-C(sp3)–H amidation of alkylimidates: facile synthesis of 1,2-amino alcohols

X. Mou, X. Chen, G. Chen and G. He, Chem. Commun., 2018, 54, 515 DOI: 10.1039/C7CC08897C

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