Issue 54, 2018
From the journal:

Chemical Communications

Zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration†

Xin-Qi Zhu,a   Qing Sun,b   Zhi-Xin Zhang,a   Bo Zhou,a   Pei-Xi Xie,a   Wen-Bo Shen,a   Xin Lu,*b   Jin-Mei Zhoua  and  Long-Wu Ye ORCID logo *ac  

* Corresponding authors

a iChEM, State Key Laboratory of Physical Chemistry of Solid Surfaces and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China
E-mail: longwuye@xmu.edu.cn

b iChEM, State Key Laboratory of Physical Chemistry of Solid Surfaces, and Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China
E-mail: xinlu@xmu.edu.cn

c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Abstract

A novel zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration has been developed, which represents the first example of a non-noble metal-catalyzed reaction between isoxazoles and alkynes. This method allows the facile and atom-economical synthesis of a range of valuable β-keto enamides. Moreover, the computational study provides further evidence for the feasibility of the proposed reaction mechanism.

Graphical abstract: Zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration

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Article information

DOI
https://doi.org/10.1039/C8CC03140A
Article type
Communication
Submitted
18 Apr 2018
Accepted
15 May 2018
First published
16 May 2018

Chem. Commun., 2018,54, 7435-7438

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Zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration

X. Zhu, Q. Sun, Z. Zhang, B. Zhou, P. Xie, W. Shen, X. Lu, J. Zhou and L. Ye, Chem. Commun., 2018, 54, 7435 DOI: 10.1039/C8CC03140A

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