Metal‐Free Oxyacetoxylation of Arylynamines and Ynamides To Construct α‐Acetoxyl Amides-Reference-Cited by-同舟云学术

Metal‐Free Oxyacetoxylation of Arylynamines and Ynamides To Construct α‐Acetoxyl Amides

Published:2023-07-26 Issue:32 Volume:26 Page:
ISSN:1434-193X
Container-title:European Journal of Organic Chemistry
language:en
Short-container-title:Eur J Org Chem

Author:

Long Rong¹,Huang Shaoling¹,Wu Han‐Kui²³,Iqbal Naila²,Wu Na²^ORCID

Affiliation:

1. Chongqing Key Laboratory of Green Synthesis and Applications College of Chemistry Chongqing Normal University Chongqing 401331 P. R. China

2. School of Chemistry and Biosciences Faculty of Life Sciences University of Bradford Bradford West Yorkshire BD7 1DP United Kingdom

3. College of Biology and Food Engineering Anyang Institute of Technology Anyang Henan Province 455000 P. R. China

Abstract

AbstractYnamides/arylynamines are challenging substrates for oxyacetoxylation, especially due to various reactive sites of the N‐heteroaryl ring. Herein, we report a metal‐free PhI(OAc)2‐mediated oxyacetoxylation of arylynamines/ynamides to provide α‐acetoxyl amides in good to excellent yields. The transformation completes in a short time to afford solely the product in a highly regio‐ and chemo‐selective manner through β‐iodo keteneiminium intermediate, without functionalising the N‐heteroaryl moiety.

Funder

Natural Science Foundation of Guangxi Zhuang Autonomous Region

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

Reference86 articles.

2. Alkaloids from Strychnos henningsii

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5. Evaluation of canthinone alkaloids as cerebral protective agents

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