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Rh-Catalyzed tandem C–C/C–N bond formation of quinoxalines with alkynes leading to heterocyclic ammonium salts

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Abstract

An efficient Rh-catalyzed oxidative C–H activation/annulation of 2-arylquinoxalines with internal alkynes is described using Cu(OAc)2·H2O and AgBF4 to afford a diverse variety of substituted quarternary ammonium salts at room temperature. The mechanism of the protocol is established on the basis of isolation of the 5-membered rhodacycle intermediate and kinetic isotope studies. The mild reaction conditions, substrate scope and functional group diversity are the salient practical features.

Graphical abstract: Rh-Catalyzed tandem C–C/C–N bond formation of quinoxalines with alkynes leading to heterocyclic ammonium salts

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Publication details

The article was received on 14 Dec 2018, accepted on 24 Jan 2019 and first published on 24 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB03103G
Citation: Org. Biomol. Chem., 2019, Advance Article

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    Rh-Catalyzed tandem C–C/C–N bond formation of quinoxalines with alkynes leading to heterocyclic ammonium salts

    K. Talukdar, S. Roy, R. Bag and T. Punniyamurthy, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB03103G

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