Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 52, Pages 18859-18863Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910871
Keywords
homogeneous catalysis; fluoride; multifunctional reagents; palladium; sulfur
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Funding
- Croucher Foundation
- EPSRC
- EPSRC [EP/K024205/1] Funding Source: UKRI
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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.
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