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Synthesis and Activity of Six-Membered Cyclic Alkyl Amino Carbene–Ruthenium Olefin Metathesis Catalysts

Samkian, Adrian E. and Xu, Yan and Virgil, Scott C. and Yoon, Ki-Young and Grubbs, Robert H. (2020) Synthesis and Activity of Six-Membered Cyclic Alkyl Amino Carbene–Ruthenium Olefin Metathesis Catalysts. Organometallics, 39 (4). pp. 495-499. ISSN 0276-7333. https://resolver.caltech.edu/CaltechAUTHORS:20200206-125057818

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Abstract

Ru–cyclic alkyl amino carbene (Ru–CAAC) olefin metathesis catalysts perform extraordinarily in metathesis macrocyclization and ethenolysis, but previous studies have been limited to the use of five-membered CAAC (CAAC-5) ligands. In this work, we synthesized a different group of ruthenium catalysts with more σ-donating and π-accepting six-membered CAAC (CAAC-6) ligands, and their metathesis activity was probed through initiation studies, ring-closing metathesis (RCM), cross-metathesis, and ethenolysis. These catalysts display higher initiation rates than analogous Ru–CAAC-5 complexes but demonstrate lower activity in RCM and ethenolysis.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.organomet.9b00862DOIArticle
ORCID:
AuthorORCID
Samkian, Adrian E.0000-0002-0068-3572
Xu, Yan0000-0003-2808-7964
Virgil, Scott C.0000-0001-8586-5641
Yoon, Ki-Young0000-0003-3257-6103
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2020 American Chemical Society. Received: December 23, 2019; Published: February 6, 2020. We gratefully acknowledge Umicore for financial support and donation of HG1. Dr. Adam Johns is acknowledged for insightful suggestions and discussions. Dr. Mona Shahgoli is acknowledged for assistance with acquiring mass spectra. Dr. William Wolf, Dr. Jeong Hoon Ko, and Dr. Jianchun Wang are acknowledged for helpful discussions. A.E.S. and Y.X. contributed equally. The authors declare no competing financial interest. Accession Codes: CDC 1972385−1972386 contain the supplementary rystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; fax: +44 1223 336033.
Funders:
Funding AgencyGrant Number
Umicore N.V.UNSPECIFIED
Issue or Number:4
Record Number:CaltechAUTHORS:20200206-125057818
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200206-125057818
Official Citation:Synthesis and Activity of Six-Membered Cyclic Alkyl Amino Carbene–Ruthenium Olefin Metathesis Catalysts. Adrian E. Samkian, Yan Xu, Scott C. Virgil, Ki-Young Yoon, and Robert H. Grubbs. Organometallics 2020 39 (4), 495-499; DOI: 10.1021/acs.organomet.9b00862
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:101172
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:07 Feb 2020 17:32
Last Modified:28 Feb 2020 19:12

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