Transition Metal‐Free<i>O</i>‐Arylation of<i>N</i>‐Alkoxybenzamides Enabled by Aryl(trimethoxyphenyl)iodonium Salts-Reference-Cited by-同舟云学术

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

Published:2023-07-04 Issue:16 Volume:365 Page:2703-2710
ISSN:1615-4150
Container-title:Advanced Synthesis & Catalysis
language:en
Short-container-title:Adv Synth Catal

Author:

Elboray Elghareeb E.¹²,Bae Taeho¹,Kikushima Kotaro¹,Kita Yasuyuki³,Dohi Toshifumi¹³^ORCID

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 chemoselectiveO‐versus 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

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202300406

Reference146 articles.

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