储玲玲:Ligand-controlled stereodivergent alkenylation of alkynes to access functionalized trans- and cis-1,3-dienes
发布人:张妮  发布时间:2024-04-02   

Abstract: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.


原文链接:https://www.nature.com/articles/s41467-022-35688-2