Journal
GREEN CHEMISTRY
Volume 19, Issue 7, Pages 1740-1750Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7gc00267j
Keywords
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Funding
- National Natural Science Foundation of China [21572162, 21472140]
- Natural Science Foundation of Zhejiang Province [LY16B020012]
- Science and Technology Project of Zhejiang Province [2016C31022]
- Xinmiao Talent Planning Foundation of Zhejiang Province [2016R426058, 2016R426059]
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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(sp(3))-cyano group and subsequent intramolecular cyclization findings that were further supported by density functional theory (DFT) calculations.
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