Ligand-controlled stereodivergent alkenylation of alkynes to access functionalized trans- and cis-1,3-dienes.
Tianyu LongChen ZhuLing LiLiang ShaoShengqing ZhuMagnus RuepingLingling ChuPublished in: Nature communications (2023)
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.
Keyphrases
- reduced graphene oxide
- metal organic framework
- molecular docking
- quantum dots
- crystal structure
- photodynamic therapy
- molecularly imprinted
- visible light
- carbon nanotubes
- oxide nanoparticles
- ionic liquid
- room temperature
- gold nanoparticles
- highly efficient
- squamous cell carcinoma
- density functional theory
- radiation therapy
- cancer therapy
- decision making
- locally advanced
- high resolution
- water soluble
- amino acid