Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

Zikun Wang; Zhansong Zhang; Wanjun Zhao; Paramasivam Sivaguru; Giuseppe Zanoni; Yingying Wang; Edward A Anderson; Xihe Bi

doi:10.1038/s41467-021-25593-5

Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

Nat Commun. 2021 Sep 2;12(1):5244. doi: 10.1038/s41467-021-25593-5.

Authors

Zikun Wang^#¹, Zhansong Zhang^#¹, Wanjun Zhao¹, Paramasivam Sivaguru¹, Giuseppe Zanoni², Yingying Wang¹, Edward A Anderson³, Xihe Bi^{4

5}

Affiliations

¹ Department of Chemistry, Northeast Normal University, Changchun, China.
² Department of Chemistry, University of Pavia, Pavia, Italy.
³ Chemistry Research Laboratory, University of Oxford, Oxford, UK.
⁴ Department of Chemistry, Northeast Normal University, Changchun, China. bixh507@nenu.edu.cn.
⁵ State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, China. bixh507@nenu.edu.cn.

^# Contributed equally.

Abstract

Sulfinyl radicals - one of the fundamental classes of S-centered radicals - have eluded synthetic application in organic chemistry for over 60 years, despite their potential to assemble valuable sulfoxide compounds. Here we report the successful generation and use of sulfinyl radicals in a dual radical addition/radical coupling with unsaturated hydrocarbons, where readily-accessed sulfinyl sulfones serve as the sulfinyl radical precursor. The strategy provides an entry to a variety of previously inaccessible linear and cyclic disulfurized adducts in a single step, and demonstrates tolerance to an extensive range of hydrocarbons and functional groups. Experimental and theoretical mechanistic investigations suggest that these reactions proceed through sequential sulfonyl and sulfinyl radical addition.

Publication types

Research Support, Non-U.S. Gov't