Silver(I)-carbene complexes/ionic liquids: Novel N-heterocyclic carbene delivery agents for organocatalytic transformations

Alan C. Sentman, Szilárd Csihony, Robert M. Waymouth, James L. Hedrick

Research output: Contribution to journalArticle

98 Citations (Scopus)

Abstract

(Chemical Equation Presented) N-Heterocyclic carbene (NHC) complexes with silver were investigated as sources of unsaturated NHC carbene catalysts via thermal decomposition. The NHC complex (1-ethyl-3-methylimidazol-2-ylidene) silver(I) chloride is an ionic liquid, and was found to catalyze the ring-opening polymerization of lactide at elevated temperatures to give narrowly dispersed polylactide of predictable molecular weight. Silver-carbene complexes can also be used for the catalysis of small molecule transesterification reactions. Thermolysis of the silver complexes in the presence of CS2 yielded the zwitter-ionic CS2 adducts of the carbene, implicating the intermediacy of the free carbene in these reactions.

Original languageEnglish
Pages (from-to)2391-2393
Number of pages3
JournalJournal of Organic Chemistry
Volume70
Issue number6
DOIs
Publication statusPublished - Mar 18 2005

ASJC Scopus subject areas

  • Organic Chemistry

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