Bronsted acid mediated N-O bond cleavage for α-amination of ketones through the aromatic nitroso aldol reaction

A Bronsted acid mediated N-O bond cleavage for a-amination of ketones has been developed through the nitroso aldol reaction of less-reactive aromatic nitroso compounds and silyl enol ethers having a disilane (-SiMe2TMS) backbone. This transformation is operationally simple and scalable, offering structurally diverse alpha-amino ketones in high yields (up to 98%) with complete regioselectivity. It represents a mechanistically unique and rare example of a metal-free N-O bond cleavage process.