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Issue 4, 2014
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Palladium-catalyzed benzo[d]isoxazole synthesis by C–H activation/[4 + 1] annulation

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Abstract

We report a palladium-catalyzed intermolecular [4 + 1] annulation pathway for N-phenoxyacetamides with aldehydes to form 1,2-benzisoxazoles. By activating the C–H bonds ortho to phenol-derived O–N bonds, the method enables the simultaneous construction of C–C and C[double bond, length as m-dash]N bonds in 1,2-benzisoxazoles with the O–N bonds intact. The method has been successfully applied to the synthesis of active pharmaceutical intermediates, such as risperidone.

Graphical abstract: Palladium-catalyzed benzo[d]isoxazole synthesis by C–H activation/[4 + 1] annulation

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Publication details

The article was received on 25 Nov 2013, accepted on 19 Dec 2013 and first published on 20 Dec 2013


Article type: Edge Article
DOI: 10.1039/C3SC53228C
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Chem. Sci., 2014,5, 1574-1578

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    Palladium-catalyzed benzo[d]isoxazole synthesis by C–H activation/[4 + 1] annulation

    P. Duan, Y. Yang, R. Ben, Y. Yan, L. Dai, M. Hong, Y. Wu, D. Wang, X. Zhang and J. Zhao, Chem. Sci., 2014, 5, 1574
    DOI: 10.1039/C3SC53228C

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