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Issue 10, 2018
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Copper catalyzed cyanation through C[double bond, length as m-dash]C bond cleavage of gem-aryl dibromide followed by second cyanation of iodoarene by a released CN unit

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Abstract

A new approach for the synthesis of aryl cyanides through C[double bond, length as m-dash]C cleavage of styrenyl gem-dibromide via an in situ cyanation process by sodium azide in the presence of CuO nanoparticles and simultaneous intermolecular cyanation of an iodoarene by capturing a released CN unit has been achieved. Several diversely substituted aryl/heteroaryl cyanides including a precursor to etravirine, a drug for the treatment of HIV, have been obtained by this procedure. This protocol is unique with regard to cyanation without a cyanide reagent and provides access to two different nitriles in one reaction involving full utilization of CN units.

Graphical abstract: Copper catalyzed cyanation through C [[double bond, length as m-dash]] C bond cleavage of gem-aryl dibromide followed by second cyanation of iodoarene by a released CN unit

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Publication details

The article was received on 31 Jan 2018, accepted on 12 Mar 2018 and first published on 13 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QO00108A
Citation: Org. Chem. Front., 2018,5, 1586-1599
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    Copper catalyzed cyanation through C[double bond, length as m-dash]C bond cleavage of gem-aryl dibromide followed by second cyanation of iodoarene by a released CN unit

    P. Maity, D. Kundu, T. Ghosh and B. C. Ranu, Org. Chem. Front., 2018, 5, 1586
    DOI: 10.1039/C8QO00108A

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