Method for the analysis of free carbenes present after NHC-organocatalyzed transformations

TitleMethod for the analysis of free carbenes present after NHC-organocatalyzed transformations
Publication TypeJournal Article
Year of Publication2017
AuthorsDas, TKanti, Biju, AT
JournalEuropean Journal of Organic Chemistry
Issue30
Pagination4500-4506
Date PublishedAUG
Type of ArticleArticle
Abstract

In N-heterocyclic carbene (NHC) based organocatalysis, usually, the free carbene is generated in situ by treatment of the azolium salt with a base. Described herein is a method for the analysis of the NHC present in the reaction flask after the NHC-organocatalyzed reaction. For this, the reaction mixture was treated with elemental sulfur after the reaction and the thus-formed thiourea/thione derivative was isolated. Common NHC-catalyzed transformations such as benzoin reactions, Stetter reactions, homoenolate annulation reactions, and reactions proceeding via the ,-unsaturated acylazolium intermediate have been studied. The results indicate that after the reactions, 28-84% of the initial carbenes exist in the free form.

DOI10.1002/ejoc.201700903
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.068

Divison category: 
Organic Chemistry