Volume 58, Issue 33 pp. 11439-11443
Communication

Iron(II)-Based Metalloradical Activation: Switch from Traditional Click Chemistry to Denitrogenative Annulation

Satyajit Roy

Satyajit Roy

Division of Molecular Synthesis & Drug Discovery, Centre of Bio-Medical Research (CBMR), SGPGIMS Campus, Raebareli Road, Lucknow, 226014 U.P., India

These authors contributed equally to this work.

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Hillol Khatua

Hillol Khatua

Division of Molecular Synthesis & Drug Discovery, Centre of Bio-Medical Research (CBMR), SGPGIMS Campus, Raebareli Road, Lucknow, 226014 U.P., India

These authors contributed equally to this work.

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Sandip Kumar Das

Sandip Kumar Das

Division of Molecular Synthesis & Drug Discovery, Centre of Bio-Medical Research (CBMR), SGPGIMS Campus, Raebareli Road, Lucknow, 226014 U.P., India

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Prof. Dr. Buddhadeb Chattopadhyay

Corresponding Author

Prof. Dr. Buddhadeb Chattopadhyay

Division of Molecular Synthesis & Drug Discovery, Centre of Bio-Medical Research (CBMR), SGPGIMS Campus, Raebareli Road, Lucknow, 226014 U.P., India

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First published: 11 June 2019
Citations: 73

Graphical Abstract

1,2,3,4: A unique intermolecular denitrogenative annulation of 1,2,3,4-tetrazoles and alkynes was discovered by employing a catalytic amount of Fe(TPP)Cl and Zn dust. This reaction precludes the traditional click reaction between organic azides and alkynes.

Abstract

A unique concept for the intermolecular denitrogenative annulation of 1,2,3,4-tetrazoles and alkynes was discovered by using a catalytic amount of Fe(TPP)Cl and Zn dust. The reaction precludes the traditional, more favored click reaction between an organic azide and alkynes, and instead proceeds by an unprecedented metalloradical activation. The method is anticipated to advance access to the construction of important basic nitrogen heterocycles, which will in turn enable discoveries of new drug candidates.

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