Transition Metal‐FreeO‐Arylation ofN‐Alkoxybenzamides Enabled by Aryl(trimethoxyphenyl)iodonium Salts

Author:

Elboray Elghareeb E.12,Bae Taeho1,Kikushima Kotaro1,Kita Yasuyuki3,Dohi Toshifumi13ORCID

Affiliation:

1. Graduate School of Pharmaceutical Sciences Ritsumeikan University 1-1-1, Nojihigashi Kusatsu Shiga 525-8577 Japan

2. Department of Chemistry Faculty of Science South Valley University Qena 83523 Egypt

3. Research Organization of Science and Technology Ritsumeikan University 1-1-1, Nojihigashi Kusatsu Shiga 525-8577 Japan

Abstract

AbstractHerein, we develop a metal catalyst‐free protocol forO‐arylation of benzamide hydroxamate esters. The chemoselectiveOversus N‐arylation of the amides was tuned by varying the electronic and/or steric properties of the diaryliodonium salt and/or the substrate. TheO‐arylation reaction would preferentially occur for sterically and electronically diverse substrates. This study, which reveals the possibility of substituent‐ and reagent‐controlled chemoselectivity, with diaryliodonium salts might attract interest in the area of hypervalent iodine chemistry.

Publisher

Wiley

Subject

General Chemistry

Reference146 articles.

1. See for example:

2. A. Greenberg C. M. Breneman J. F. Liebman (Ed.) in The Amide Linkage: Structural Significance in Chemistry Biochemistry and Materials Science New York: Wiley 2000;

3. The Medicinal Chemist’s Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates

4. Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?

5. Analysis of the reactions used for the preparation of drug candidate molecules

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