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...

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Bibliographic Details
Published in:Organic letters 2021-04, Vol.23 (7), p.2797-2801
Main Authors: Bajohr, Jonathan, Diallo, Abdoul G, Whyte, Andrew, Gaillard, Sylvain, Renaud, Jean-Luc, Lautens, Mark
Format: Article
Language:English
Subjects:
Catalysis
Chemical Sciences
Material chemistry
Organic chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00716