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Related Concept Videos

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

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.
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution01:17

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
Carbocations02:10

Carbocations

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...
Reactions of Carboxylic Acids: Introduction01:41

Reactions of Carboxylic Acids: Introduction

Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.
Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the π bonding...
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is activated by...

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Organic small-molecule-catalyzed carbonylation reactions.

Mao-Lin Yang1, Le-Cheng Wang1,2, Heifei Yang1,2

  • 1Leibniz-Institut für Katalyse e.V. Albert-Einstein-Str. 29a 18059 Rostock Germany Xiao-Feng.Wu@Catalysis.de xwu2020@dicp.ac.cn.

Chemical Science
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Summary

Organic small molecules, particularly N-heterocyclic carbenes, are emerging as powerful catalysts for carbonylation reactions. This review highlights their potential to advance sustainable chemical synthesis beyond traditional metal catalysts.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Sustainable Chemistry

Background:

  • C1 chemistry is crucial for academic and industrial applications, traditionally relying on metal catalysts.
  • Organic small-molecule catalysts offer advantages for carbonylation reactions, presenting an attractive alternative.
  • Exploring novel catalytic systems is key to advancing sustainable chemical synthesis.

Purpose of the Study:

  • To review organic small-molecule-catalyzed carbonylation reactions.
  • To emphasize the role of N-heterocyclic carbene (NHC) catalysis.
  • To explore main-group species-based catalysts for sustainable carbonylation.

Main Methods:

  • Literature review of organic small-molecule-catalyzed carbonylation.
  • Focus on N-heterocyclic carbene (NHC) catalysts.
  • Examination of oxygen, sulfur, selenium, nitrogen, and phosphine-based catalysts.

Main Results:

  • Organic small molecules, especially NHCs, show significant promise in catalyzing carbonylation.
  • Main-group element catalysts expand the scope of sustainable carbonylation.
  • Carbonylation reactions can be viewed as catalyst-designed processes.

Conclusions:

  • Organic small-molecule catalysis offers a sustainable and versatile approach to carbonylation.
  • NHC and main-group catalysts are key players in advancing this field.
  • Future developments in organic small molecule catalysis will drive innovation in carbonylation chemistry.