Palladium-Catalyzed Domino Heck/Sulfination: Synthesis of Sulfonylated Hetero- and Carbocyclic Scaffolds Using DABCO-Bis(sulfur dioxide)

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.

Automated summary

A Pd-catalyzed domino Heck/SO2 insertion reaction has been reported for the synthesis of a variety of hetero- and carbocyclic scaffolds. The reaction utilizes DABSO as a safe and easy-to-handle alternative to SO2 gas, proceeding through a sulfinate intermediate for the generation of sulfones, sulfonamides, and sulfonyl fluorides in situ. Good yields and scalability have been demonstrated.