Ligand-controlled stereodivergent alkenylation of alkynes to access functionalized trans- and cis-1,3-dienes

Tianyu Long, Chen Zhu, Ling Li, Liang Shao, Shengqing Zhu, Magnus Rueping () and Lingling Chu ()
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Tianyu Long: Donghua University, College of Chemistry and Chemical Engineering
Chen Zhu: King Abdullah University of Science and Technology (KAUST), KAUST Catalysis Center (KCC)
Ling Li: Donghua University, College of Chemistry and Chemical Engineering
Liang Shao: Donghua University, College of Chemistry and Chemical Engineering
Shengqing Zhu: Donghua University, College of Chemistry and Chemical Engineering
Magnus Rueping: King Abdullah University of Science and Technology (KAUST), KAUST Catalysis Center (KCC)
Lingling Chu: Donghua University, College of Chemistry and Chemical Engineering

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: 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.

Date: 2023
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DOI: 10.1038/s41467-022-35688-2

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