Copper-Catalyzed Carbonylative Cross-Coupling of Alkyl Iodides with Alcohols and Sodium Hydroxide: Synthesis of Esters and Carboxylic Acids

Omaïma Adaoudi; Julie Le Bescont; Antoine Bruneau-Voisine; Gwilherm Evano

doi:10.1055/a-2042-3417

Synthesis, Table of Contents

Synthesis 2024; 56(04): 668-676
DOI: 10.1055/a-2042-3417

special topic

Synthetic Development of Key Intermediates and Active Pharmaceutical Ingredients (APIs)

Copper-Catalyzed Carbonylative Cross-Coupling of Alkyl Iodides with Alcohols and Sodium Hydroxide: Synthesis of Esters and Carboxylic Acids

Omaïma Adaoudi

^aLaboratoire de Chimie Organique, Service de Chimie et Physico-Chimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium

,

Julie Le Bescont

^aLaboratoire de Chimie Organique, Service de Chimie et Physico-Chimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium

,

Antoine Bruneau-Voisine

^bOril Industrie, 13 rue Auguste Desgenétais, CS 60125, 76210 Bolbec, France

,

Gwilherm Evano ∗

^aLaboratoire de Chimie Organique, Service de Chimie et Physico-Chimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium

› Author Affiliations

Abstract

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Abstract

A general and inexpensive catalytic system is reported for the copper-catalyzed carbonylative coupling between alkyl iodides and alcohols or sodium hydroxide. Upon reaction with catalytic amounts of copper(I) chloride and N,N,N′,N′′,N′′-pentamethyldiethylenetriamine under a mild pressure of carbon monoxide (5 bar), a range of secondary and tertiary alkyl iodides are readily converted into the corresponding esters and carboxylic acids without competing direct nucleophilic substitution. Main advantages of this procedure include its broad applicability, the use of an especially inexpensive and available catalytic system, and its user-friendliness.

Key words

copper catalysis - cross-coupling - carbonylation - carbon monoxide - esters - carboxylic acids

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References

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Supplementary Material

Supporting Information