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Efficient solvent- and temperature-tuned access to aldoxime ethers and phenolic functions by Pd-catalyzed C–O cross-coupling of aldoximes with aryl bromides and bromo-chalcones

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Abstract

A single method with a functionality switching option was developed for the first time for the Pd-catalyzed C–O cross-coupling of aryl bromides and bromo-chalcones with aldoximes. The ligand tBuXPhos (L2) was found to be an effective supporting ligand for the Pd-catalyzed coupling of aldoximes with bromo coupling partners. The functionality switching from oxime ethers to a phenolic or hydroxy group was driven by solvent or temperature. This method offers the products in good to excellent yields in short reaction times.

Graphical abstract: Efficient solvent- and temperature-tuned access to aldoxime ethers and phenolic functions by Pd-catalyzed C–O cross-coupling of aldoximes with aryl bromides and bromo-chalcones

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Article information


Submitted
11 Oct 2019
Accepted
15 Dec 2019
First published
06 Jan 2020

New J. Chem., 2020, Advance Article
Article type
Paper

Efficient solvent- and temperature-tuned access to aldoxime ethers and phenolic functions by Pd-catalyzed C–O cross-coupling of aldoximes with aryl bromides and bromo-chalcones

Reeta, T. M. Rangarajan, K. Kaushik, R. P. Singh, M. Singh and R. P. Singh, New J. Chem., 2020, Advance Article , DOI: 10.1039/C9NJ05124D

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