Experimental and theoretical studies on cycloaddition (3 + 2) reactions of azides to nitro-olefins

Nitroolefins have emerged as important building blocks for the synthesis of 1,2,3-triazoles, representing an important advance in the search for more efficient and selective alternatives of these units.1 Several types of reactional systems have been used highlighting the possibility of direct use of sodium azides (leading to the preparation of 1H-1,2,3-triazoles) as well as substituted azides and nitroolefins giving substituted 1,2,3-triazoles. With the introduction of organocatalysis and metal catalysis in these systems, the control of the regioselectivity of this reaction has been described.2 However, no more in-depth mechanistic study has been described so far.3 Therefore, this work aims to investigate the (3 + 2) cycloaddition reaction of nitroolefins using computational techniques (predict energies and mechanisms with or without catalysis, using polar and apolar solvents, etc) and kinetic studies. Herein we present initial results.