Palladium-Catalyzed Domino Heck/Sulfination: Synthesis of Sulfonylated Hetero- and Carbocyclic Scaffolds Using DABCO–Bis(sulfur dioxide)
Jonathan Bajohr, Abdoul G. Diallo, Andrew Whyte, Sylvain Gaillard, Jean‐Luc Renaud, Mark Lautens
Abstract
The synthesis of a broad variety of hetero- and carbocyclic scaffolds via a Pd-catalyzed domino Heck/SO2 insertion reaction is reported. This reaction utilizes DABSO, a safe and easy-to-handle alternative to SO2 gas. The reaction proceeds through a sulfinate intermediate, which can act as a lynchpin for the in situ generation of sulfones, sulfonamides, and sulfonyl fluorides. Good yields and scalability are demonstrated.
Topics & Concepts
ChemistryDominoDABCOCatalysisPalladiumSulfur dioxideCombinatorial chemistrySulfurReaction conditionsOrganic chemistrySulfonylAlkylSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions