Access to Polysulfides through Photocatalyzed Dithiosulfonylation

• Published in: Angewandte Chemie International Edition Vol. 62; no. 25; pp. e202302199 - n/a
• Main Authors: Ren, Xiaorui, Ke, Qiumin, Zhou, Yuanyuan, Jiao, Jingchao, Li, Guoxin, Cao, Si, Wang, Xuyong, Gao, Qianwen, Wang, Xi
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 19-06-2023
• Edition: International ed. in English
• Subjects: Alkenes; Alkynes; Atom economy; Catalysis; Disulfuration; Indicators and Reagents; Olefins; Photocatalysis; Polyenes; Radicals; Reagents; Regioselectivity; Stereoselectivity; Styrene; Substrates; Synthetic Methods; Synthetic Methods; Disulfuration; Olefins; Photocatalysis; Radicals
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202302199

In this study, we outline a general method for photocatalyzed difunctionalization of alkenes, a diene, alkynes, 1,3‐enynes, and [1.1.1]propellane using dithiosulfonate reagents (ArSO2‐SSR) with improved atom economy. Both “ArSO2‐” and “‐SSR” on the dithiosulfonate are transferred under mild conditions with broad substrate scope, high stereoselectivity, and complete regioselectivity. Significantly, the resulting dithiosulfonylated styrene is a general and practical nucleophilic disulfuration reagent, reacting with a variety of electrophiles efficiently. Both reactions can be conducted on gram scale, rendering the approach highly valuable.
Herein, we report a general photocatalyzed difunctionalization of alkenes, alkynes, 1,3‐enynes, and [1.1.1]propellane with dithiosulfonates. The resulting dithiosulfonylated styrene is an excellent nucleophilic disulfuration reagent, which can react with a variety of electrophiles to access unsymmetric disulfides efficiently.