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

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.