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September 10, 2025

Photoinduced Ligated Boryl Radical-Mediated Alkynylation of Inert Iodoalkanes

Key Points

This method enables the formation of diverse substituted alkynes through a radical pathway, enhancing synthetic capabilities.
Utilizing ligated boranes as XAT reagents, the transformation activates various inert alkyl iodides efficiently.
Mild reaction conditions allow for the incorporation of multiple functional groups in the target molecules.
Preliminary mechanistic insights suggest a radical mechanism underlying the reaction, highlighting innovative synthetic pathways.

Abstract

In this study, we report a metal-free C(sp3)-C(sp) cross-coupling reaction between chemically inert alkyl iodides and arylacetylene bromides. This transformation utilizes bench-stable, ligated boranes as a halogen atom transfer (XAT) reagent to activate various alkyl iodides. The mild and straightforward reaction conditions enable the efficient synthesis of a broad array of substituted alkynes, accommodating diverse functional groups. Furthermore, the synthetic utility of the method has been showcased through the successful late-stage alkynylation of several pharmaceutically relevant molecules. Preliminary mechanistic investigations indicate that the transformation proceeds via a radical pathway.

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Cite This Study

Bisoyi et al. (Thu,) studied this question.

synapsesocial.com/papers/68c1a90c54b1d3bfb60e2231 https://doi.org/https://doi.org/10.1021/acs.orglett.5c02783

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