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 11月 2017
Accepted
13 12月 2017
First published
13 12月 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements