The Shuttle of Sulfur Dioxide: Iridium/Copper‐Cocatalyzed Trifluoromethylfluorosulfonylation of Alkenes

• Published in: Advanced synthesis & catalysis Vol. 365; no. 3; pp. 301 - 306
• Main Authors: Yang, Yi‐Fei, Xiao, Fang, Lin, Jin‐Hong, Xiao, Ji‐Chang
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 07.02.2023; Wiley Subscription Services, Inc
• Subjects: Alkenes; Chemistry; Chemistry, Applied; Chemistry, Organic; Copper; fluorosulfonylation; Functional groups; Iridium; one-pot two-step; Physical Sciences; pyridinium salt; Science & Technology; SO2 shuttle; Sulfur dioxide; synergistic catalysis; SO2 shuttle; one-pot two-step; synergistic catalysis; HYDROCARBONS; CARBON BOND ACTIVATION; fluorosulfonylation; pyridinium salt
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.202201286

Depending on the nature of the attached functional moiety, the sulfonyl radical can either undergo an automatic SO2 liberation or react directly as the thermodynamically favored sulfonyl radical. Taking advantage of this unique property, we envisioned that through rational reaction design, the in situ release and re‐insertion of SO2, i. e., the shuttle of SO2, can be realized. Herein we report our recent progress in copper metallaphotoredox co‐catalyzed trifluoromethyl‐fluorosulfonylation of alkenes with TFSP as both the CF3 and SO2 source. Valuable functional groups are added across the double bonds. Besides, A wide array of synthetically useful moieties featuring distinct electronic patterns and various nitrogenous heterocycles are well tolerated by this strategy.