Issue 5, 2019

Dehydroxylated amination accompanied by 1,2-sulfur immigration

Abstract

A sulfur neighbouring-group participation N-alkylation method is presented, which enables the simultaneous C–O cleavage, C–S immigration and C–N formation performed in a metal free system. The method has considerable generality and proceeds with excellent selectivity. Particularly noteworthy is the finding that the synergetic mechanism attributes to enhance both chemoselectivity and regioselectivity for this C–N coupling, which is distinguished from traditional nucleophilic mechanism.

Graphical abstract: Dehydroxylated amination accompanied by 1,2-sulfur immigration

Supplementary files

Article information

Article type
Research Article
Submitted
08 Nov 2018
Accepted
09 Jan 2019
First published
10 Jan 2019

Org. Chem. Front., 2019,6, 643-647

Dehydroxylated amination accompanied by 1,2-sulfur immigration

Y. Cui, T. Lu, Z. Shi and J. Feng, Org. Chem. Front., 2019, 6, 643 DOI: 10.1039/C8QO01211C

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