Issue 16, 2023

Sulfonyl radical-triggered two/three-component tandem bicyclization of CN-containing 1,6-enynes under transition metal- and base-free conditions

Abstract

Radical tandem bicyclization provides a novel approach for the preparation of complex polycyclic compounds in synthetic chemistry. Herein, we first described a tandem radical bicyclization reaction of CN-containing 1,6-enynes with sulfonyl hydrazides by using tert-butyl hydroperoxide (TBHP) as the oxidant under metal- and base-free conditions. To expand the synthetic utility of our protocol, we then proposed a more practical three-component reaction of 1,6-enynes, aryldiazoniums and Na2S2O5 without any additives, generating the sulfonyl radical via the rapid insertion of sulfur dioxide (SO2) using cheap and non-toxic Na2S2O5. These two protocols feature several merits including transition metal- and base-free conditions, step- and atom-economical reaction modes, remarkably broad substrate scope, and capability of scaling up to the gram scale.

Graphical abstract: Sulfonyl radical-triggered two/three-component tandem bicyclization of CN-containing 1,6-enynes under transition metal- and base-free conditions

Supplementary files

Article information

Article type
Research Article
Submitted
09 Jun 2023
Accepted
14 Jul 2023
First published
15 Jul 2023

Org. Chem. Front., 2023,10, 4139-4145

Sulfonyl radical-triggered two/three-component tandem bicyclization of CN-containing 1,6-enynes under transition metal- and base-free conditions

H. Qiu, L. Li, X. Cai, M. Li, Y. Lu, L. Wang, K. Tang, H. Liu, J. Chen and W. Wei, Org. Chem. Front., 2023, 10, 4139 DOI: 10.1039/D3QO00865G

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