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Published January 11, 2012 | Supplemental Material + Accepted Version
Journal Article Open

Improved Ruthenium Catalysts for Z-Selective Olefin Metathesis


Several new C–H-activated ruthenium catalysts for Z-selective olefin metathesis have been synthesized. Both the carboxylate ligand and the aryl group of the N-heterocyclic carbene have been altered and the resulting catalysts evaluated using a range of metathesis reactions. Substitution of bidentate with monodentate X-type ligands led to a severe attenuation of metathesis activity and selectivity, while minor differences were observed between bidentate ligands within the same family (e.g., carboxylates). The use of nitrato-type ligands in place of carboxylates afforded a significant improvement in metathesis activity and selectivity. With these catalysts, turnover numbers approaching 1000 were possible for a variety of cross-metathesis reactions, including the synthesis of industrially relevant products.

Additional Information

© 2011 American Chemical Society. Received: October 31, 2011. Publication Date (Web): November 19, 2011. Lawrence Henling and Dr. Michael Day are acknowledged for X-ray crystallographic analysis. Dr. David VanderVelde is thanked for assistance with NMR experimentation and analysis. This work was financially supported by the NIH (NIH 5R01GM031332-27), the NSF (CHE-1048404), Mitsui Chemicals, Inc. (K.E.), and the NDSEG (fellowship to B.K.K.). Instrumentation on which this work was carried out were supported by the NSF (X-ray diffractometer, CHE-0639094) and the NIH (NMR spectrometer, RR027690). Materia, Inc. is thanked for its donation of metathesis catalysts.

Attached Files

Accepted Version - nihms343610.pdf

Supplemental Material - ja210225e_si_001.pdf

Supplemental Material - ja210225e_si_002.cif


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August 19, 2023
October 24, 2023