Issue 3, 2023
From the journal:

Organic Chemistry Frontiers

Catalytic site-specific and regioselective (3 + 2) transannulations between 1,2,3-thiadiazoles and allenoates†

Cunzhi Chen,a   Shuyan Fang,a   Mingwu Yu, ORCID logo b   Jiaxi Xu ORCID logo a  and  Zhanhui Yang ORCID logo *a  

* Corresponding authors

a Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P. R. China
E-mail: zhyang@mail.buct.edu.cn

b School of Chemistry and Materials Science, Ludong University, Yantai, Shandong 264025, P. R. China

Abstract

Allenoates, a type of perpendicularly “strained” surrogate of alkynes, readily transannulate, site-specifically and regio-selectively, with 1,2,3-thiadiazoles in the presence of catalytic Rh(I)/bisphosphine, producing tetrasubstituted thiophenes in a redox-neutral manner. 1,2,3-Thiadiazoles act as masked 1,3-dipoles with nucleophilic sulfur and electrophilic carbon termini.

Graphical abstract: Catalytic site-specific and regioselective (3 + 2) transannulations between 1,2,3-thiadiazoles and allenoates

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Article information

DOI
https://doi.org/10.1039/D2QO01662A
Article type
Research Article
Submitted
20 Oct 2022
Accepted
22 Nov 2022
First published
23 Nov 2022

Org. Chem. Front., 2023,10, 661-667

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Catalytic site-specific and regioselective (3 + 2) transannulations between 1,2,3-thiadiazoles and allenoates

C. Chen, S. Fang, M. Yu, J. Xu and Z. Yang, Org. Chem. Front., 2023, 10, 661 DOI: 10.1039/D2QO01662A

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