Journal
ORGANIC LETTERS
Volume 23, Issue 7, Pages 2797-2801Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00716
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Funding
- Natural Science and Engineering Research Council (NSERC)
- Kennarshore, Inc.
- LABEX Syn Org [ANR-11-LABX-0029]
- Walter C. Sumner Memorial Fellowship
- Province of Ontario (QEII)
- University of Toronto
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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.
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.
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