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Published January 21, 2022 | Supplemental Material
Journal Article Open

Bulky Cyclometalated Ruthenium Nitrates for Challenging Z‐Selective Metathesis: Efficient One‐Step Access to α‐Oxygenated Z‐Olefins from Acrylates and Allyl Alcohols


α-Oxygenated Z-olefins are ubiquitous in biologically active molecules and serve as versatile handles for organic synthesis, but their syntheses are often tedious and less selective. Here we report the efficient Z-selective metathesis of various terminal acrylates and allyl alcohols, which enables facile and selective construction of high value-added α-oxygenated Z-olefins from readily available feedstock chemicals. These challenging metathesis transformations are enabled by novel cyclometalated Ru-carbene-nitrate complexes bearing bulky-yet-flexible side arms, whose assembly was unlocked by new organometallic syntheses.

Additional Information

© 2021 Wiley-VCH. Issue Online: 14 January 2022; Version of Record online: 07 December 2021; Accepted manuscript online: 14 November 2021; Manuscript received: 27 September 2021. We gratefully acknowledge Umicore for financial support. This research was benefited from the use of instrumentation made available by the Caltech CCE Multiuser Mass Spectrometry Laboratory, and Dr. Mona Shahgoli is thanked for assistance with HRMS experiments. Dr. Adam Johns and Dr. Jianchun Wang are acknowledged for helpful discussions. The authors declare no conflict of interest.

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August 22, 2023
October 23, 2023