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Issue 20, 2017
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Palladium-catalyzed tandem addition/cyclization in aqueous medium: synthesis of 2-arylindoles

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Abstract

An efficient protocol to construct 2-arylindoles was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover, the utility of this catalytic tandem transformation was also demonstrated in an efficient gram-scale synthesis. This method provides an alternative synthetic tool for accessing a more diverse array of 2-arylindoles.

Graphical abstract: Palladium-catalyzed tandem addition/cyclization in aqueous medium: synthesis of 2-arylindoles

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Publication details

The article was received on 07 Mar 2017, accepted on 20 Mar 2017 and first published on 30 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00572E
Citation: Org. Biomol. Chem., 2017,15, 4300-4307
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    Palladium-catalyzed tandem addition/cyclization in aqueous medium: synthesis of 2-arylindoles

    S. Yu, K. Hu, J. Gong, L. Qi, J. Zhu, Y. Zhang, T. Cheng and J. Chen, Org. Biomol. Chem., 2017, 15, 4300
    DOI: 10.1039/C7OB00572E

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