Multiple Roles of Isocyanides in Palladium-Catalyzed Imidoylative Couplings: A Mechanistic Study

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TitreMultiple Roles of Isocyanides in Palladium-Catalyzed Imidoylative Couplings: A Mechanistic Study
Type de publicationJournal Article
Year of Publication2016
AuteursPerego LA, Fleurat-Lessard P, Kaim LEl, Ciofini I, Grimaud L
JournalCHEMISTRY-A EUROPEAN JOURNAL
Volume22
Pagination15491-15500
Date PublishedOCT
Type of ArticleArticle
ISSN0947-6539
Mots-clésCoupling, insertion, isocyanide, Palladium, reaction mechanisms
Résumé

{Kinetic, spectroscopic and computational studies examining a palladium-catalyzed imidoylative coupling highlight the dual role of isocyanides as both substrates and ligands for this class of transformations. The synthesis of secondary amides from aryl halides and water is presented as a case study. The kinetics of the oxidative addition of ArI with RNC-ligated Pd-0 species have been studied and the resulting imidoyl complex [(ArC=NR)Pd(CNR)(2)I] (Ar=4-F-C6H4

DOI10.1002/chem.201602913