Precise stereocontrol of functionalized alkenes represents a long-standing research topic in organic synthesis. Nevertheless, the development of a catalytic, easily tunable synthetic approach for the stereodivergent synthesis of both E-selective and even more challenging Z-selective highly substituted 1,3-dienes from common substrates remains underexploited. Here, we report a photoredox and nickel dual catalytic strategy for the stereodivergent sulfonylalkenylation of terminal alkynes with vinyl triflates and sodium sulfinates under mild conditions. With a judicious choice of simple nickel catalyst and ligand, this method enables efficient and divergent access to both Z- and E-sulfonyl-1,3-dienes from the same set of simple starting materials. This method features broad substrate scope, good functional compatibility, and excellent chemo-, regio-, and stereoselectivity. Experimental and DFT mechanistic studies offer insights into the observed divergent stereoselectivity controlled by ligands.
Bibliographical noteKAUST Repository Item: Exported on 2023-01-06
Acknowledged KAUST grant number(s): URF/1/4025
Acknowledgements: The authors are grateful for the financial support provided by the National Natural Science Foundation of China (21971036), the National Science Fund for Excellent Young Scholars (22122101), the Shanghai Rising-Star Program (20QA1400200), the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4025). The authors acknowledge the KAUST Supercomputing Laboratory for providing the computational resources of the Shaheen-II supercomputer.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Physics and Astronomy(all)