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Gong J, Hu K, Shao Y, et al. Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles. Org Biomol Chem. 2020;18(3):488-494doi: 10.1039/c9ob02408e.
Gong, J., Hu, K., Shao, Y., Li, R., Zhang, Y., Hu, M., & Chen, J. (2020). Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles. Organic & biomolecular chemistry, 18(3), 488-494. https://doi.org/10.1039/c9ob02408e
Gong, Julin, et al. "Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles." Organic & biomolecular chemistry vol. 18,3 (2020): 488-494. doi: https://doi.org/10.1039/c9ob02408e
Gong J, Hu K, Shao Y, Li R, Zhang Y, Hu M, Chen J. Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles. Org Biomol Chem. 2020 Jan 22;18(3):488-494. doi: 10.1039/c9ob02408e. PMID: 31850443.
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Org Biomol Chem. 2020 Jan 22;18(3):488-494. doi: 10.1039/c9ob02408e.

Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles.

Organic & biomolecular chemistry

Julin Gong, Kun Hu, Yinlin Shao, Renhao Li, Yetong Zhang, Maolin Hu, Jiuxi Chen

Affiliations

  1. College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. China. [email protected] [email protected].

PMID: 31850443 DOI: 10.1039/c9ob02408e

Abstract

The first example of the palladium-catalyzed tandem addition/cyclization of 2-(2-acylphenoxy)acetonitriles with arylboronic acids has been developed, providing a new strategy for the synthesis of 2-aroyl benzofurans with excellent chemoselectivity and wide functional group compatibility. Preliminary mechanistic experiments indicate that this tandem process involves sequential nucleophilic addition generating 2-(2-acylphenoxy)-1-phenylethan-1-one followed by an intramolecular cyclization. This methodology has also been applied to the synthesis of 2-aroyl indoles and the potent CYP19 inhibitor 1-(benzofuran-2-yl(phenyl)methyl)-1H-1,2,4-triazole.

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