Bisoyi Akash, Tripathy Alisha Rani, Poolamanna Ramsiya, Yatham Veera Reddy
School of Chemistry, Indian Institute of Science Education and Research, Thiruvananthapuram 695551, India.
Org Lett. 2025 Aug 15;27(32):9042-9048. doi: 10.1021/acs.orglett.5c02783. Epub 2025 Jul 31.
In this study, we report a metal-free C(sp)-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.
在本研究中，我们报道了一种在化学惰性的烷基碘化物和芳基乙炔溴化物之间进行的无金属C(sp)-C(sp)交叉偶联反应。这种转化利用易于操作的、连接的硼烷作为卤原子转移（XAT）试剂来活化各种烷基碘化物。温和且简便的反应条件能够高效合成一系列含有各种官能团的取代炔烃。此外，该方法的合成实用性已通过几个与药物相关分子的成功后期炔基化得到了展示。初步机理研究表明，该转化通过自由基途径进行。
