Issue 20, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
07 Mar 2017
Accepted
20 Mar 2017
First published
30 Mar 2017

Org. Biomol. Chem., 2017,15, 4300-4307

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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