Issue 6, 2014

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
27 Feb 2014
Accepted
09 May 2014
First published
12 May 2014

Org. Chem. Front., 2014,1, 657-660

Author version available

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

X. Yan, X. Yi and C. Xi, Org. Chem. Front., 2014, 1, 657 DOI: 10.1039/C4QO00056K

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