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Published January 25, 2010 | Supplemental Material + Accepted Version
Journal Article Open

Ruthenium Olefin Metathesis Catalysts Bearing Carbohydrate-Based N-Heterocyclic Carbenes


Ru-based olefin metathesis catalysts containing carbohydrate-derived NHCs from glucose and galactose were synthesized and characterized by NMR spectroscopy. 2D-NMR spectroscopy revealed the presence of Ru−C (benzylidene) rotamers at room temperature, and the rate of rotation was measured using magnetization transfer and VT-NMR spectroscopy. The catalysts were found to be effective at ring-opening metathesis polymerization (ROMP), ring-closing metathesis (RCM), cross-metathesis (CM), and asymmetric ring-opening cross-metathesis (AROCM) and showed surprising selectivity in both CM and AROCM.

Additional Information

© 2010 American Chemical Society. Received October 5, 2009; publication Date (Web): December 18, 2009. We thank Dr. David VanderVelde and Prof. Dan O'Leary for assisting with the 2D-NMR characterization and line shape analysis, respectively, and thank both for helpful discussions. We also thank Prof. Brian Stoltz for the use of his groups' Chiral HPLC. We gratefully acknowledge the financial support of the NSF and NIH (Grant No. 5R01 GM31332), and B.K.K. thanks the NDSEG for a graduate fellowship. Finally, we thank Materia, Inc., for a generous donation of ruthenium complex 1.

Attached Files

Accepted Version - nihms166527.pdf

Supplemental Material - om900864r_si_001.pdf


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