The Selective Nickel-Catalyzed N-Allylation of C3-Unprotected Indoles under Mild and Clean Conditions

A simple salt free and selective N-allylation of indoles with allylic alcohols has been developed. The protocol uses a catalytic amount of a nickel complex generated in situ from Ni(cod)(2) and dppf as diphosphine. The use of DMSO as the reaction solvent is crucial to control the regioselectivity of the reaction with the exclusive formation of the N-allyl product among up to three possible products.

Automated summary

A simple salt-free and selective N-allylation reaction of indoles with allylic alcohols has been developed using a catalytic amount of a nickel complex generated in situ from Ni(cod)(2) and dppf as diphosphine. The regioselectivity of the reaction is controlled by using DMSO as the reaction solvent, exclusively forming the N-allyl product among up to three possible products.