Palladium-Catalyzed [3+2+2] Cycloaddition Between Carbonyl-Tethered Alkylidenecyclopropanes and Isocyanates

IF 1.5 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Helvetica Chimica Acta Pub Date : 2025-02-20 DOI:10.1002/hlca.202500011

Ricardo Rodiño, Jose L. Mascareñas, Fernando López

引用次数: 0

Abstract

Carbonyl-tethered alkylidenecyclopropanes can react with aryl isocyanates in presence of Pd(0)-phosphoramidite catalysts to give seven-membered heterobicyclic products in a formal [3+2+2] cycloaddition process. The reaction involves the formation of a palladium π-allyl complex intermediate (A), which behaves as a formal 1,5-dipole, and can be trapped by externally added isocyanates. This report also includes preliminary assays of asymmetric variants, as well as DFT computational studies that shed some light on the nature of the catalytic cycle.

查看原文本刊更多论文

钯催化羰基系链烷基环丙烷与异氰酸酯之间的[3+2+2]环加成反应

羰基系链烷基环丙烷可以在Pd(0)-酰胺磷催化剂的存在下与芳基异氰酸酯反应，以正式的[3+2+2]环加成反应生成七元杂环产物。该反应包括钯π-烯丙基络合物中间体(a)的形成，该中间体表现为形式的1,5偶极子，可以被外部添加的异氰酸酯捕获。该报告还包括对不对称变体的初步分析，以及DFT计算研究，这些研究揭示了催化循环的本质。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Helvetica Chimica Acta 化学-化学综合

CiteScore

3.00

自引率

0.00%

发文量

审稿时长

2.3 months

期刊介绍： Helvetica Chimica Acta, founded by the Swiss Chemical Society in 1917, is a monthly multidisciplinary journal dedicated to the dissemination of knowledge in all disciplines of chemistry (organic, inorganic, physical, technical, theoretical and analytical chemistry) as well as research at the interface with other sciences, where molecular aspects are key to the findings. Helvetica Chimica Acta is committed to the publication of original, high quality papers at the frontier of scientific research. All contributions will be peer reviewed with the highest possible standards and published within 3 months of receipt, with no restriction on the length of the papers and in full color.