通过钯催化的脱羧烯丙基烷基化反应合成3,3-二取代烯丙基异吲哚啉酮
Synthesis of 3,3-Disubstituted Allyl Isoindolinones via Pd-Catalyzed Decarboxylative Allylic Alkylation.
作者信息
Alvarado Mario, Loo Marisa, Adler Hanna, Arnall Caroline, Amsden Katharine, Martinez Gisela, Navarro Raul
机构信息
Department of Chemistry, Occidental College, Los Angeles, California 90041, United States.
出版信息
Tetrahedron Lett. 2024 Sep 19;148. doi: 10.1016/j.tetlet.2024.155242. Epub 2024 Aug 3.
Abstract
Herein, we report a mild palladium-catalyzed decarboxylative allylic alkylation of allyl ester-substituted isoindolinone substrates to afford a variety of 3,3-disubstituted isoindolinone derivatives. The decarboxylative coupling reaction tolerates a range of functional groups, including ketones and alkenyl halides, and does not require protection of the isoindolinone nitrogen. Additionally, the reaction was found to proceed in near-quantitative yield for most substrates evaluated. Based on the isolation of competing cyclopropane and protonation products, a reaction mechanism is proposed.
摘要
在此，我们报道了一种温和的钯催化烯丙基酯取代异吲哚啉酮底物的脱羧烯丙基烷基化反应，以得到多种3,3-二取代异吲哚啉酮衍生物。该脱羧偶联反应能耐受一系列官能团，包括酮和卤代烯烃，并且不需要对异吲哚啉酮氮进行保护。此外，发现该反应对大多数评估的底物都能以接近定量的产率进行。基于竞争性环丙烷和质子化产物的分离，提出了一种反应机理。
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