Ghosh Suman, Kumar Shailendra, Chakrabortty Rajesh, Ganesh Venkataraman
Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, West Bengal 721302, India.
Org Lett. 2024 Aug 9;26(31):6574-6579. doi: 10.1021/acs.orglett.4c02109. Epub 2024 Jul 29.
Here, we report a general copper-catalyzed C(sp) carboboration of 1,3-diynes, providing access to an array of tetra-substituted boryl enynes in a regioselective manner. All four positions of enyne can be efficiently manipulated using this methodology. The reaction was smoothly applied in the conjugation of complex bioactive molecules to the enyne scaffold. Cross-coupling reactions were carried out with boron end groups on densely substituted 1,3-enynes, opening avenues for the modular synthesis of highly functionalized enynes. Control experiments and density functional theory studies supported the proposed mechanism.
在此，我们报道了一种通用的铜催化1,3 - 二炔的C(sp)碳硼化反应，该反应能够以区域选择性的方式合成一系列四取代的硼基烯炔。利用这种方法可以有效地对烯炔的所有四个位置进行操控。该反应顺利地应用于将复杂生物活性分子与烯炔支架进行共轭连接。在高度取代的1,3 - 烯炔上带有硼端基的情况下进行了交叉偶联反应，为模块化合成高度官能化的烯炔开辟了道路。对照实验和密度泛函理论研究支持了所提出的反应机理。
