Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China.
J Org Chem. 2023 Mar 3;88(5):2973-2984. doi: 10.1021/acs.joc.2c02691. Epub 2023 Feb 14.
A highly efficient heterogeneous copper(I)-catalyzed cross-coupling of trialkylsilylethynes with -tosylhydrazones has been achieved in dioxane at 90-110 °C via the Cu carbene migratory insertion with an SBA-15-immobilized l-proline-Cu(I) complex [SBA-15-l-Proline-CuI] as the catalyst and LiOBu as the base, leading to the formation of C(sp)-C(sp) bonds. The reaction generates a wide variety of alkyltrialkylsilylalkynes in moderate to high yields. This new heterogenized copper(I) complex exhibits a comparable catalytic efficiency to homogeneous CuI and can be easily recovered through a simple centrifugation process and is recyclable up to 12 times without a remarkable loss of activity.
一种高效的异相铜（I）催化三烷基硅基炔与对甲苯磺酰腙的交叉偶联反应，在 90-110°C 的二氧六环中，通过 SBA-15 固载的 l-脯氨酸-Cu（I）配合物[SBA-15-l-脯氨酸-CuI]作为催化剂和 LiOBu 作为碱，实现了铜卡宾的迁移插入，生成 C(sp)-C(sp)键。该反应以中等至高产率生成了多种烷基三烷基硅基炔。这种新型的固载铜（I）配合物表现出与均相 CuI 相当的催化效率，可以通过简单的离心过程容易地回收，并可重复使用 12 次以上，活性没有明显损失。
