Details

Autor(en) / Beteiligte

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

Titel

Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

Ist Teil von

• Nature communications, 2021-09, Vol.12 (1), p.5244-5244, Article 5244

Ort / Verlag

London: Nature Publishing Group UK

Erscheinungsjahr

2021

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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. Sulfinyl radicals are an underexplored synthon in organic chemistry due to the fact that they reversibly add to pi systems and undergo homodimerization. Here the authors synthesize sulfonyl sulfones, previously thought to be unstable, and demonstrate their broad use as sulfinyl radical precursors in disulfurizations of alkenes and alkynes.