Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

Zikun Wang, Zhansong Zhang, Wanjun Zhao, Paramasivam Sivaguru, Giuseppe Zanoni, Yingying Wang, Edward A. Anderson and Xihe Bi ()
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Zikun Wang: Northeast Normal University
Zhansong Zhang: Northeast Normal University
Wanjun Zhao: Northeast Normal University
Paramasivam Sivaguru: Northeast Normal University
Giuseppe Zanoni: University of Pavia
Yingying Wang: Northeast Normal University
Edward A. Anderson: University of Oxford
Xihe Bi: Northeast Normal University

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: 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.

Date: 2021
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DOI: 10.1038/s41467-021-25593-5

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