Isocyanide-Based One-Pot Cascade Synthesis of 3-Acyl Isoindolinones
作者机构：Key Laboratory of Organic Synthesis of Jiangsu ProvinceCollege of ChemistryChemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and TechnologySoochow UniversitySuzhouJiangsu215123 China Suzhou Baolidi Functional Materials Research InstituteSuzhouJiangsu215144 China
出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)
年 卷 期：2024年第42卷第3期
页 面：259-263页
核心收录：
学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学]
基 金：the National Natural Science Foundation of China(Nos.21772138 and 21672157) the Natural Science Foundation of Jiangsu Province(BK20221356) PAPD
主 题：One-pot reaction Isocyanide Pd catalysis Rearrangement reaction Isoindolinone
摘 要：A series of 3-acyl-substituted isoindolinone derivatives were synthesized in a one-pot manner via the reaction of o-bromobenzaldehydes,isocyanides,and carboxylic acids in the presence of palladium catalyst and base. The reaction employing easily available starting materials features simple operation and high efficiency. The mechanistic study showed that the reaction might undergo 1) Pd-catalyzed [3+2] cyclization of o-bromobenzaldehyde with isocyanide and the re-insertion of another molecule of isocyanide,2) addition of carboxylic acid to in situ formed ketenimine followed by a rearrangement relay to give 3,3-diacyl-substituted isoindolinone derivative. Further transformations of the obtained products through decarbonylation could also be realized.
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