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Cyclic Alkenylsulfonyl Fluorides: Palladium‐Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents
Author(s) -
Lou Terry ShingBong,
Bagley Scott W.,
Willis Michael C.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201910871
Subject(s) - reagent , palladium , surface modification , electrophile , derivatization , chemistry , catalysis , combinatorial chemistry , sulfonyl , sulfur , organic chemistry , alkyl , high performance liquid chromatography
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.