Bifunctional Sodium Dithionite Promoted Radical-Polar Crossover Cyclization: Diversified Synthesis of Functionalized Cyclic Sultines

Cheng-Jing Li; Meng-Yu Liu; Zhong-Lin Wei; Wei-Wei Liao

doi:10.1021/acs.joc.4c02606

Bifunctional Sodium Dithionite Promoted Radical-Polar Crossover Cyclization: Diversified Synthesis of Functionalized Cyclic Sultines

J Org Chem. 2024 Dec 20;89(24):18769-18774. doi: 10.1021/acs.joc.4c02606. Epub 2024 Dec 11.

Authors

Cheng-Jing Li¹, Meng-Yu Liu¹, Zhong-Lin Wei¹, Wei-Wei Liao^{1

2}

Affiliations

¹ Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P R China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P R China.

PMID: 39661929
DOI: 10.1021/acs.joc.4c02606

Abstract

A catalyst-free reductive radical-polar crossover cyclization with alkenes and sodium dithionite to construct densely functionalized cyclic sultines was described. The key to the success of this practical protocol relies not only on a bifunctional role of sodium dithionite, that is, serving as radical initiator and SO₂ source, but also on the diversified conversions (RPCC/SO₂ insertion/S_N2 cyclization and RPCC/SO₂ insertion/1,4-addition cyclization processes), which enabled efficient construction of target compounds with the high efficiency and atom- and step-economy under mild conditions.