In(0)/Cu(I)-Mediated Alkylation of Imines in Aqueous Media

Significance

The direct addition of alkyl organometallic to imines is known to be a challenging reaction. A Barbier-Grignard-type alkylation of imines with secondary alkyl iodides in water, as reported here, is a good alternative. The imines are obtained in situ from aldehydes and amines. Both aliphatic and aromatic aldehydes can be successfully used. A diastereoselective variant of this reaction, using an enantiopure amine, is also described. The mild condition and simplicity makes this method attractive for scale-up processes.