Direct cleavage of the NN bond of azobenzenes by MeOTf leading to N-arylbenzimidazoles?

Organic Chemistry Frontiers Pub Date: 2014-05-12 DOI: 10.1039/C4QO00056K

Abstract

Direct cleavage of the N[double bond, length as m-dash]N bond of azo compounds by methyltriflate (MeOTf) leading to benzimidazoles has been described. In this reaction, the MeOTf serves as one carbon unit and inserts into the N[double bond, length as m-dash]N bond to form benzimidazole via cleavage of the N[double bond, length as m-dash]N bond and three C–H bonds and meanwhile formation of three C–N bonds.

Graphical abstract: Direct cleavage of the N [[double bond, length as m-dash]] N bond of azobenzenes by MeOTf leading to N-arylbenzimidazoles
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