General Palladium-Catalyzed Cross Coupling of Cyclopropenyl Esters

IF 7.6 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chemical Science Pub Date : 2025-05-30 DOI:10.1039/d5sc03096j

Zachary P. Sercel, Ilan Marek

引用次数: 0

Abstract

We report a method for the direct palladium-catalyzed cross coupling reactions of cyclopropenyl esters bearing a variety of substitution patterns with Csp² 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.

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钯催化环丙烯酯的交叉偶联

我们报道了一种直接钯催化的环丙烯酯与Csp2碘化物具有多种取代模式的交叉偶联反应的方法。这种反应在很大程度上对耦合伙伴的电子性质不敏感。醋酸四甲基铵是一种卤化物螯合剂，作为有机碱特别有效。观察到的KIE为2.5，表明C-H键的裂解参与了限制转化率的步骤。这种方法使环丙烯的快速组装成为可能，而环丙烯的制备以前需要使用有毒的锡和砷试剂。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemical Science CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

4.80%

发文量

1352

审稿时长

2.1 months

期刊介绍： Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.