Turning sulfonyl and sulfonimidoyl fluoride electrophiles into sulfur(VI) radicals for alkene ligation

Xing Wu, Wenbo Zhang, Guangwu Sun, Xi Zou, Xiaoru Sang, Yongmin He and Bing Gao ()
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Xing Wu: Hunan University
Wenbo Zhang: Hunan University
Guangwu Sun: Hunan University
Xi Zou: Hunan University
Xiaoru Sang: Hunan University
Yongmin He: Hunan University
Bing Gao: Hunan University

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract Sulfonyl and sulfonimidoyl fluorides are versatile substrates in organic synthesis and medicinal chemistry. However, they have been exclusively used as S(VI)+ electrophiles for defluorinative ligations. Converting sulfonyl and sulfonimidoyl fluorides to S(VI) radicals is challenging and underexplored due to the strong bond dissociation energy of SVI−F and high reduction potentials, but once achieved would enable dramatically expanded synthetic utility and downstream applications. In this report, we disclose a general platform to address this issue through cooperative organosuperbase activation and photoredox catalysis. Vinyl sulfones and sulfoximines are obtained with excellent E selectivity under mild conditions by coupling reactions with alkenes. The synthetic utility of this method in the preparation of functional polymers and dyes is also demonstrated.

Date: 2023
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DOI: 10.1038/s41467-023-40615-0

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