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Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zhongyi Zeng, Abigail Feceu, Nardana Sivendran, Lukas J. Gooßen

2021Advanced Synthesis & Catalysis117 citationsDOIOpen Access PDF

Abstract

Abstract Carboxylic acids are among the most used feedstock chemicals due to their great structural diversity and easy handling. The use of carboxylic acids and their derivatives in decarboxylative couplings has proven to be a valuable tool for the construction of C−C and C‐heteroatom bonds. This synthetic strategy provides a complementary bond disconnection to traditional cross‐coupling methods. In this review, we provide a comprehensive overview of decarboxylation‐initiated intermolecular C‐heteroatom bond formation, outlining several main mechanistic concepts combined with early examples and highlighting the achievements made in the past decade until January 2021. In these reactions, carboxylic acids and their derivatives undergo initial decarboxylation and then react with other heteroatom electrophiles and nucleophiles, thus replacing the carboxylate group with a valuable and prevalent heteroatom functionality. magnified image

Topics & Concepts

DecarboxylationChemistryHeteroatomElectrophileNucleophileCarboxylateIntermolecular forceOrganic chemistryCombinatorial chemistryCatalysisMoleculeRing (chemistry)Catalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques