Catalyst-Free Alkylation of Quinoxalines in Water

Abstract A catalyst-free nucleophilic allylation of quinoxalines in water has been developed, enabling efficient synthesis of versatile, functionalized C3-alkylated quinoxalin-2(1H)-ones. This method selectively activates the imine moiety through hydrogen-bonding interactions, shunning conventional strategies that require transition metals, photoirradiation, or elevated temperatures. Remarkably, the reaction exhibits accelerated kinetics in water, due to strong hydrogen-bonding effects that facilitate reactant aggregation.