Metal-free aminocarbonylation of p-quinone methides with isocyanides: synthesis of sterically hindered alpha-arylated acetamides

TitleMetal-free aminocarbonylation of p-quinone methides with isocyanides: synthesis of sterically hindered alpha-arylated acetamides
Publication TypeJournal Article
Year of Publication2022
AuthorsShirsath, SR, More, DA, Muthukrishnan, M
JournalChemistry-an Asian Journal
Volume17
Issue20
Paginatione202200642
Date PublishedOCT
Type of ArticleArticle
ISSN1861-4728
KeywordsAminocarbonylation, Isocyanide, p-Quinone methide, Sterically Hindered alpha-Arylated Acetamides
Abstract

The synthesis of sterically hindered alpha-arylated acetamides generally requires a multistep reaction sequence and is also difficult to access due to steric constraints. This protocol allows the synthesis of sterically hindered alpha-arylated acetamides in moderate to high yields via 1,6-addition of isocyanides to p-quinone methides in the presence of BF3 center dot OEt2. The present transformation features transition metal-free conditions, avoiding the use of toxic carbon monoxide, broad substrate scope, mild reaction conditions, and operational simplicity.

DOI10.1002/asia.202200642
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.839

Divison category: 
Organic Chemistry
Database: 
Web of Science (WoS)

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