Insights on the Petasis Borono–Mannich multicomponent reaction mechanism

Abstract

A joint experimental and theoretical investigation on the mechanism of the Petasis Borono–Mannich reaction is described. Using the charge-tag strategy for mass spectrometry ion monitoring in solution, unprecedented key intermediates were intercepted and characterized. A key intermediate was also isolated from the reaction solution and its structure could be deduced from single crystal X-ray diffraction. A mechanism further consolidated by DFT calculations that reconciles the present and all available data on this important multicomponent reaction is presented.