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Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

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Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...

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Metal-Catalyzed Decarboxylative C-H Functionalization.

Ye Wei^1,2, Peng Hu^1,3, Min Zhang¹

¹State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences , Fuzhou, Fujian 350002, China.

Chemical Reviews

|March 8, 2017

Summary

This summary is machine-generated.

Decarboxylative C-H functionalization combines C-H activation and decarboxylation for novel organic synthesis. This review covers recent advances in functionalizing Csp-H, Csp2-H, and Csp3-H bonds for diverse compound synthesis.

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

C-H bond activation and decarboxylation are fundamental reactions in organic synthesis.
Combining these processes yields decarboxylative C-H functionalization, a powerful synthetic strategy.

Purpose of the Study:

To provide a comprehensive overview of decarboxylative C-H functionalization.
To highlight recent advances and applications in synthesizing various organic compounds.

Main Methods:

Review of literature on decarboxylative C-H functionalization.
Analysis of functionalization across Csp-H, Csp2-H, and Csp3-H bonds.

Main Results:

Demonstrates the utility of decarboxylative C-H functionalization in synthesizing styrenes, chalcones, biaryls, and heterocycles.
Covers scopes, limitations, practical applications, and synthetic potentials of these reactions.

Conclusions:

Decarboxylative C-H functionalization is a versatile and rapidly advancing field in organic synthesis.
This methodology offers significant potential for creating complex organic molecules efficiently.