Issue 8, 2022

Metal-free regioselective cascade sulfonylation–cyclization of 3-aza-1,5-enynes with sulfur dioxide and aryldiazonium tetrafluoroborates to construct 1,2-dihydropyridines

Abstract

Radical cascade cyclization of tethered alkynes has emerged as an efficient tool to construct small but complex cyclic compounds. However, it currently relies on aryl or heteroaryl-tethered alkynes to give benzene-fused molecules. Herein, we describe a regioselective cascade cyclization of vinyl-tethered alkynes, 3-aza-1,5-enynes. This method features good functional group compatibility and mild conditions and provides an environmentally friendly way to construct 1,2-dihydropyridines.

Graphical abstract: Metal-free regioselective cascade sulfonylation–cyclization of 3-aza-1,5-enynes with sulfur dioxide and aryldiazonium tetrafluoroborates to construct 1,2-dihydropyridines

Supplementary files

Article information

Article type
Research Article
Submitted
09 Feb 2022
Accepted
09 Mar 2022
First published
10 Mar 2022

Org. Chem. Front., 2022,9, 2228-2233

Metal-free regioselective cascade sulfonylation–cyclization of 3-aza-1,5-enynes with sulfur dioxide and aryldiazonium tetrafluoroborates to construct 1,2-dihydropyridines

R. Ding, Y. Deng, S. Luo, X. Tang, L. Liu and P. Wang, Org. Chem. Front., 2022, 9, 2228 DOI: 10.1039/D2QO00175F

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