☆ 4.7 Article

2-Arylacetamides as Versatile Precursors for 3-Aminoisocoumarin and Homophthalimide Derivatives: Palladium-Catalyzed Cascade Double Carbonylation Reactions

ADVANCED SYNTHESIS & CATALYSIS (2016)

期刊

ADVANCED SYNTHESIS & CATALYSIS

卷 358, 期 16, 页码 2692-2700

出版社

WILEY-V C H VERLAG GMBH

DOI: 10.1002/adsc.201600224

关键词

carbonylation; cascade reactions; C-H functionalization; heterocycles; palladium

类别

Chemistry, Applied Chemistry, Organic

资金

Spanish Ministerio de Economia y Competitividad [CTQ2015-69568-P]
Fundacion Seneca [19890/GERM/15]

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Protocol

Reagent

摘要

The synthesis of biologically relevant homophthalimide and 3-aminoisocoumarin nuclei via palladium-catalyzed carbonylation of 2-(2-iodoaryl) acetamides has been developed. The degree of N-substitution on the starting amide substrate dictates whether C-N or C-O coupling takes place in the final step of the catalytic cycle giving rise to each type of heterocycle. The introduction of a second C-halogen bond in the starting acetamides allows a catalytic cascade double carbonylation involving a C-H activation step to give fused heterocyclic structures.

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