Divergent functionalization of α,β-enones: catalyst-free access to β-azido ketones and β-amino α-diazo ketones

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.

Automated summary

A method for azidation of beta-fluoroalkyl alpha,beta-unsaturated ketones has been developed, allowing access to a wide variety of fluorinated nitrogenous carbonyl compounds. The strategy does not involve any metallic or organic catalysts, and the choice of solvents can modulate the reaction outcomes to produce either beta-azido ketones or beta-amino alpha-diazo ketones. The reaction system is environmentally friendly, operates under mild conditions, is simple, and exhibits excellent functional group tolerance.