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Published December 16, 2020 | Supplemental Material
Journal Article Open

Efficient Z-Selective Olefin-Acrylamide Cross-Metathesis Enabled by Sterically Demanding Cyclometalated Ruthenium Catalysts


The efficient Z-selective cross-metathesis between acrylamides and common terminal olefins has been developed by the use of novel cyclometalated ruthenium catalysts with bulky N-heterocyclic carbene (NHC) ligands. Superior reactivity and stereoselectivity are realized for the first time in this challenging transformation, allowing streamlined access to an important class of cis-Michael acceptors from readily available feedstocks. The kinetic preference for cross-metathesis is enabled by a pivalate anionic ligand, and the origin of this effect is elucidated by density functional theory calculations.

Additional Information

© 2020 American Chemical Society. Received: October 28, 2020; Published: December 4, 2020. We gratefully acknowledge Umicore and National Science Foundation (Grant CHE-1764328 to K.N.H.) for financial support. Dr. Adam Johns is acknowledged for insightful suggestions. Dr. Ki-Young Yoon is acknowledged for assistance with crystallographic data. Dr. William Wolf, Dr. Jiaming Li, and Dr. Jianchun Wang are acknowledged for helpful discussions. Calculations were performed on the Hoffman2 cluster at the University of California, Los Angeles, and the Extreme Science and Engineering Discovery Environment (XSEDE), which is supported by the National Science Foundation (Grant OCI-1053575). The authors declare no competing financial interest.

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Supplemental Material - ja0c11334_si_001.cif

Supplemental Material - ja0c11334_si_002.pdf


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