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Palladium-catalyzed direct mono-aroylation of O-arylmethyl and aryl-substituted acetoxime ethers

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Abstract

An efficient palladium-catalyzed ortho-aroylation of O-arylmethyl and aryl-substituted acetoxime ethers has been developed; this method has high mono-site selectivity and does not require exogenous ligands. Under the direction of a simple exo-acetoxime auxiliary, a broad scope of masked arylmethyl alcohols and phenols as well as various aromatic aldehydes are compatible with this transformation, which probably follows a mechanistic pathway involving a six- or five-membered exo-cyclopalladated intermediate. The strategy can be expediently adopted to prepare synthetically valuable 1H-benzo[d][1,2]oxazines and benzo[d]isoxazoles. The directing group can be easily removed from the products to afford the functionalized diaryl ketones.

Graphical abstract: Palladium-catalyzed direct mono-aroylation of O-arylmethyl and aryl-substituted acetoxime ethers

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Publication details

The article was received on 13 Jun 2018, accepted on 02 Aug 2018 and first published on 03 Aug 2018


Article type: Paper
DOI: 10.1039/C8OB01400K
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Palladium-catalyzed direct mono-aroylation of O-arylmethyl and aryl-substituted acetoxime ethers

    L. Shao, Z. Xu, C. Wang, X. Fu, M. Chen, H. Liu and Y. Ji, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01400K

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