Sercel Zachary P, Marek Ilan
Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis, Technion - Israel Institute of Technology Technion City Haifa 3200009 Israel
Chem Sci. 2025 May 30;16(26):12162-12167. doi: 10.1039/d5sc03096j. eCollection 2025 Jul 2.
We report a method for the direct palladium-catalyzed cross coupling reactions of cyclopropenyl esters bearing a variety of substitution patterns with Csp iodides. This reaction is largely insensitive to the electronic nature of the coupling partner. Tetramethylammonium acetate, a halide sequestrant, was exceptionally effective as an organic base. An observed KIE of 2.5 revealed C-H bond cleavage to be involved in the turnover-limiting step. This method enables the rapid assembly of cyclopropenes whose preparation previously required the use of toxic tin and arsenic reagents.
我们报道了一种直接钯催化的、带有各种取代模式的环丙烯酯与Csp碘化物的交叉偶联反应方法。该反应对偶联伙伴的电子性质基本不敏感。卤化物螯合剂乙酸四甲基铵作为有机碱表现出特别的效果。观察到的2.5的动力学同位素效应（KIE）表明C-H键断裂参与了限速步骤。这种方法能够快速组装环丙烯，而其制备以前需要使用有毒的锡和砷试剂。
