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

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.

Automated summary

A general and inexpensive catalytic system for copper-catalyzed carbonylative coupling between alkyl iodides and alcohols or sodium hydroxide has been reported. Under mild pressure of carbon monoxide (5 bar) and catalytic amounts of copper(I) chloride and N,N,N',N?,N?-pentamethyldiethylenetriamine, a variety of secondary and tertiary alkyl iodides are easily converted into the corresponding esters and carboxylic acids without competing direct nucleophilic substitution. The main advantages of this procedure include broad applicability, the use of an especially inexpensive and available catalytic system, and user-friendliness.