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Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

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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Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

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Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
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Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
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Carbocations02:10

Carbocations

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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Aminocarbonylation using CO surrogates.

Kamya Rao1, Anku Sharma1, Gajanan K Rathod1

  • 1Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Sector 67, S. A. S. Nagar, Punjab, 160 062, India. rahuljain@niper.ac.in.

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This review explores safer alternatives to toxic carbon monoxide (CO) gas for aminocarbonylation reactions. CO surrogates improve safety, expand substrate scope, and simplify amide bond formation processes.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Aminocarbonylation reactions are vital for synthesizing amides.
  • Traditional methods use toxic carbon monoxide (CO) gas, posing safety and handling challenges.

Purpose of the Study:

  • To review recent advancements in carbon monoxide surrogates for aminocarbonylation.
  • To highlight the benefits of using CO surrogates in terms of safety and reaction scope.

Main Methods:

  • The review examines various CO surrogates, including metal carbonyls, acids, formates, and chloroform.
  • Key methodologies, catalytic systems, and mechanistic insights are discussed.

Main Results:

  • CO surrogates offer a safer alternative to gaseous CO.
  • These substitutes enhance substrate scope and operational simplicity in aminocarbonylation.

Conclusions:

  • The use of CO surrogates significantly improves the safety and efficiency of amide bond formation.
  • CO surrogates represent a versatile advancement in synthetic organic chemistry.