Ni-Catalyzed (A + 2B)-Type Reductive Coupling of Electron-Deficient Alkenes and Alkynes through a Selective Trimerization/1,6-Reduction Cascade

Key Points

The method achieves up to 99% yield with high chemo- and stereoselectivity for dienyl esters.
Key findings include the stepwise pathway featuring selective trimerization followed by nickelacycle-mediated 1,6-reduction.
Observational analysis shows the synthetic utility in modifying bioactive molecules and developing antibacterial agents.
These findings suggest that nickel-catalyzed methods may enable future advancements in organic synthesis and pharmaceutical chemistry.

Abstract

The first nickel-catalyzed (A + 2B)-type reductive coupling of electron-deficient alkenes with alkynes has been developed. This method provides efficient access to diverse α-skipped dienyl esters in up to 99% yield with high chemo- and stereoselectivity. Synthetic utility is demonstrated in the late-stage modification of bioactive molecules and the development of antibacterial agents. Mechanistic studies indicate a stepwise pathway involving selective trimerization of alkenes with alkynes followed by a nickelacycle-mediated formal 1,6-reduction.

Bookmark

Cite This Study

Gou et al. (Tue,) studied this question.

synapsesocial.com/papers/69a75d44c6e9836116a2701a https://doi.org/https://doi.org/10.1021/acs.orglett.5c05300

Bookmark