Cyclic Alkenylsulfonyl Fluorides: Palladium‐Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents. (6th November 2019)

• Record Type: Journal Article
• Authors: Lou, Terry Shing‐Bong; Bagley, Scott W.; Willis, Michael C.
• Is Part Of: Angewandte Chemie. Volume 131:Number 52(2019)
• Page Start: 19035
• Page End: 19039
• Publication Date: 2019-11-06
• Subjects: Homogene Katalyse -- Fluoride -- Multifunktionale Reagenzien -- Palladium -- Schwefel; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201910871
• Languages: English
• ISSNs: 0044-8249

Abstract

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. Abstract : Eine Reihe von kompakten niedermolekularen cyclischen Alkenylsulfonylfluoriden kann leicht aus den entsprechenden Alkenyltriflataten über Palladiumkatalyse hergestellt werden. Diese dicht funktionalisierten Reagenzien durchlaufen eine Vielzahl von Derivatisierungsreaktionen, wie Substitution am Schwefel, Addition von Konjugaten und N‐Funktionalisierung.