Divergent Functionalization Of Alpha,Beta-Enones: Catalyst-Free Access To Beta-Azido Ketones And Beta-Amino Alpha-Diazo Ketones Dagger

A simple and practical method for the azidation of beta-fluoroalkyl alpha,beta-unsaturated ketones to access a wide variety of fluorinated nitrogenous carbonyl compounds is developed. Different from existing precedents, neither a metallic nor an organic catalyst was involved in our strategy. Judicious choice of solvents allows for the modulation of the reaction outcomes, delivering beta-azido ketones or beta-amino alpha-diazo ketones. The reaction system features environmental friendliness, mild conditions, simplicity and excellent functional group tolerance.