Issue 20, 2024

Regioselective tandem sulfonylation/cyclization of unsaturated N-substituted enamides with sulfonyl chlorides by copper catalysis

Abstract

The radical cascade cyclization of vinyl-tethered alkenes has become a promising tool for rapidly assembling nonbenzene-fused cyclic skeletons via the cracking of alkenyl C–H bonds, but this approach has been limited to 3-aza-1,5-dienes and five-membered rings have been generated. Here, we developed a radical sulfonylation/cyclization process for unsaturated N-substituted enamides with sulfonyl chlorides to form sulfonylated nonbenzene-fused six/seven-membered rings, which involved regioselective sulfonyl radical addition to the alkene and 6/7-endo cyclization.

Graphical abstract: Regioselective tandem sulfonylation/cyclization of unsaturated N-substituted enamides with sulfonyl chlorides by copper catalysis

Supplementary files

Article information

Article type
Research Article
Submitted
21 Jun 2024
Accepted
17 Aug 2024
First published
22 Aug 2024

Org. Chem. Front., 2024,11, 5784-5790

Regioselective tandem sulfonylation/cyclization of unsaturated N-substituted enamides with sulfonyl chlorides by copper catalysis

R. Ding, T. Wu, T. Ma, W. Ji, Z. Li and H. Gao, Org. Chem. Front., 2024, 11, 5784 DOI: 10.1039/D4QO01132E

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