Synthesis of highly stable 1,3-diaryl-1 H -1,2,3-triazol-5-ylidenes and their applications in ruthenium-catalyzed olefin metathesis

Jean Bouffard, Benjamin K. Keitz, Ralf Tonner, Gregorio Guisado-Barrios, Gernot Frenking, Robert H. Grubbs, Guy Bertrand

Research output: Contribution to journalArticlepeer-review

156 Scopus citations

Abstract

The formal cycloaddition between 1,3-diaza-2-azoniaallene salts and alkynes or alkyne equivalents provides an efficient synthesis of 1,3-diaryl-1H-1,2,3- triazolium salts, the direct precursors of 1,2,3-triazol-5-ylidenes. These N,N-diarylated mesoionic carbenes (MICs) exhibit enhanced stability in comparison to their alkylated counterparts. Experimental and computational results confirm that these MICs act as strongly electron-donating ligands. Their increased stability allows for the preparation of ruthenium olefin metathesis catalysts that are efficient in both ring-opening and ring-closing reactions.

Original languageEnglish
Pages (from-to)2617-2627
Number of pages11
JournalOrganometallics
Volume30
Issue number9
DOIs
StatePublished - 9 May 2011

Fingerprint

Dive into the research topics of 'Synthesis of highly stable 1,3-diaryl-1 H -1,2,3-triazol-5-ylidenes and their applications in ruthenium-catalyzed olefin metathesis'. Together they form a unique fingerprint.

Cite this