Issue 21, 2023
From the journal:

Chemical Communications

Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle–Kirmse reaction†

Fu-Yuan Yang,a   Tian-Jiao Han,a   Shi-Kun Jia,a   Min-Can Wang ORCID logo a  and  Guang-Jian Mei ORCID logo *a  

* Corresponding authors

a Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450001, China
E-mail: meigj@zzu.edu.cn

Abstract

The Sc(III)-catalyzed [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes has been established. Owing to the absence of a carbenoid intermediate, this protocol represents the first non-carbenoid variant of the Doyle–Kirmse reaction. Under mild conditions, a variety of tertiary thioethers have been readily prepared in good to excellent yields.

Graphical abstract: Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle–Kirmse reaction

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Article information

DOI
https://doi.org/10.1039/D3CC00160A
Article type
Communication
Submitted
11 Jan 2023
Accepted
13 Feb 2023
First published
13 Feb 2023

Chem. Commun., 2023,59, 3107-3110

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Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle–Kirmse reaction

F. Yang, T. Han, S. Jia, M. Wang and G. Mei, Chem. Commun., 2023, 59, 3107 DOI: 10.1039/D3CC00160A

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