Issue 4, 2014

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Nov 2013
Accepted
19 Dec 2013
First published
20 Dec 2013

Chem. Sci., 2014,5, 1574-1578

Author version available

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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