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Issue 7, 2017
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Efficient synthesis of isoquinolines in water by a Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids

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Abstract

A palladium-catalyzed tandem reaction of 2-(cyanomethyl)benzonitriles or 2-(2-carbonylphenyl)acetonitriles with arylboronic acids in water has been developed for the first time. This reaction features good functional group tolerance and provides a new strategy for the synthesis of diverse isoquinolines under mild conditions. The use of water as the reaction medium makes the synthesis process environmentally benign. Preliminary mechanistic experiments indicate that the major reaction pathway involves carbopalladation of the C(sp3)–cyano group and subsequent intramolecular cyclization findings that were further supported by density functional theory (DFT) calculations.

Graphical abstract: Efficient synthesis of isoquinolines in water by a Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids

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Publication details

The article was received on 22 Jan 2017, accepted on 02 Mar 2017 and first published on 03 Mar 2017


Article type: Paper
DOI: 10.1039/C7GC00267J
Citation: Green Chem., 2017,19, 1740-1750
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    Efficient synthesis of isoquinolines in water by a Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids

    K. Hu, L. Qi, S. Yu, T. Cheng, X. Wang, Z. Li, Y. Xia, J. Chen and H. Wu, Green Chem., 2017, 19, 1740
    DOI: 10.1039/C7GC00267J

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