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2‐Arylacetamides as Versatile Precursors for 3‐Aminoisocoumarin and Homophthalimide Derivatives: Palladium‐Catalyzed Cascade Double Carbonylation Reactions
Author(s) -
FrutosPedreño Roberto,
GarcíaLópez JoséAntonio
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600224
Subject(s) - carbonylation , chemistry , palladium , catalysis , amide , catalytic cycle , cascade , substrate (aquarium) , combinatorial chemistry , halogen , organic chemistry , carbon monoxide , oceanography , alkyl , chromatography , geology
Abstract 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.