SmI2‐mediated C‐alkylation of Ketones with Alcohols under Microwave Conditions: A Novel Route to Alkylated Ketones

A novel protocol is developed towards the preparation of alkylated ketones from alcohols in presence of catalytic amount of SmI2 and base with the elimination of water as a single by‐product under microwave irradiation conditions. Furthermore, applicability of this methodology to the synthesis of Donepezil and late‐stage functionalization in Pregnenolone is also reported. Successful application of this methodology in Friedländer quinolone synthesis using 2‐aminobenzyl alcohol and various acetophenones expand the synthetic utility of this protocol. A microwave‐assisted SmI2‐catalysed protocol has been developed for the direct C‐alkylation of ketones with alcohols. The developed methodology showed diverse substrate scope with good functional group tolerance. The methodology is also useful for the synthesis of substituted quinolines via Friedländer reaction. The synthetic applicability of the reaction is well explored by preparation of Donepezil and functionalization of Pregnenolone. Ab initio DFT studies were performed to validate the plausible mechanism.