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Published May 9, 2011 | Version Supplemental Material + Accepted Version
Journal Article Open

Synthesis of Highly Stable 1,3-Diaryl-1H-1,2,3-triazol-5-ylidenes and Their Applications in Ruthenium-Catalyzed Olefin Metathesis

Creators

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.

Additional Information

© 2011 American Chemical Society. Published In Issue May 09, 2011; Article ASAP April 13, 2011; Received: March 26, 2011. We thank Dr. Vincent Lavallo for technical assistance. Lawrence M. Henling, Dr. Michael Day, and Dr. Bruno Donnadieu are acknowledged for X-ray crystallographic analysis. We are grateful to NIH (R01 GM 68825), FQRNT (fellowship to J. B.), and NDSEG (fellowship to B.K.K.) for the financial support of this work. G.F. and R.T. acknowledge financial support of this work by the Deutsche Forschungsgemeinschaft (FR 641/26). Instrumentation facilities on which this work was carried out were supported by the NSF (CHE-0541848, CHE-0742001, CHE-0639094, and CHE-9724392), NIH (RR027690), and the AFOSR (F49620-98-1-0475).

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Accepted Version - nihms288845.pdf

Supplemental Material - om200272m_si_001.pdf

Supplemental Material - om200272m_si_002.cif

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Additional details

Identifiers

PMCID
PMC3092707
Eprint ID
23693
DOI
10.1021/om200272m
Resolver ID
CaltechAUTHORS:20110517-102330626

Related works

Describes
10.1021/om200272m (DOI)

Funding

NIH
R01 GM 68825
Fonds Québécois de la Recherche sur la Nature et les Technologies (FQRNT)
National Defense Science and Engineering Graduate (NDSEG) Fellowship
Deutsche Forschungsgemeinschaft (DFG)
FR 641/26

Dates

Created
2011-05-17
Created from EPrint's datestamp field
Updated
2021-11-09
Created from EPrint's last_modified field