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- Title
Cyclic Alkenylsulfonyl Fluorides: Palladium‐Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents.
- Authors
Lou, Terry Shing‐Bong; Bagley, Scott W.; Willis, Michael C.
- Abstract
A series of low‐molecular‐weight, compact, and multifunctional cyclic alkenylsulfonyl fluorides were efficiently prepared from the corresponding alkenyl triflates. Palladium‐catalyzed sulfur dioxide insertion using the surrogate reagent DABSO effects sulfinate formation, before trapping with an F electrophile delivers the sulfonyl fluorides. A broad range of functional groups are tolerated, and a correspondingly large collection of derivatization reactions are possible on the products, including substitution at sulfur, conjugate addition, and N‐functionalization. Together, these attributes suggest that this method could find new applications in chemical biology.
- Subjects
FLUORIDES; CHEMICAL biology; PALLADIUM; FUNCTIONAL groups; SULFUR dioxide; DERIVATIZATION
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 52, p19035
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201910871