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Atom Economy in the Metathesis Cross-Coupling of Alkenes and Alkynes

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Department of Chemistry, University at Buffalo, The State University of New York, Amherst, New York 14260, United States
Cite this: Org. Lett. 2011, 13, 11, 2896–2899
Publication Date (Web):May 11, 2011
https://doi.org/10.1021/ol200914j
Copyright © 2011 American Chemical Society

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    A cross ene-yne metathesis has been achieved at a nearly 1:1 stoichiometry of the unsaturated reactants. This allowed the use of more complex alkene reactants without sacrificing excess alkene reactant. In the alkene, different allylic oxygen protecting groups were explored. Interestingly, alkenes containing the allylic hydroxyl group proved to be the most reactive.

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    13. Martin A. Dolan, Alexandre D.C. Dixon, John D. Chisholm, Daniel A. Clark. Ruthenium dihydride complexes as enyne metathesis catalysts. Tetrahedron Letters 2018, 59 (51) , 4471-4474. https://doi.org/10.1016/j.tetlet.2018.11.016
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    15. Steven M. Swick, Sara L. Schaefer, Gregory W. O’Neil. Synthesis of the C1–C17 fragment of the archazolids by complex cis-homodimer cross metathesis. Tetrahedron Letters 2015, 56 (26) , 4039-4042. https://doi.org/10.1016/j.tetlet.2015.05.014
    16. Edgars Jecs, Steven T. Diver. Toward the synthesis of amphidinolide P: optimization of a model ene–yne metathesis fragment coupling. Tetrahedron Letters 2014, 55 (35) , 4933-4937. https://doi.org/10.1016/j.tetlet.2014.06.113
    17. Steven T. Diver, Justin R. Griffiths. Ene‐Yne Metathesis. 2014, 153-185. https://doi.org/10.1002/9781118711613.ch4
    18. S.T. Diver, J.R. Clark. 5.27 Ene–Yne Metathesis. 2014, 1302-1356. https://doi.org/10.1016/B978-0-08-097742-3.00528-0
    19. David J. Nelson, Jonathan M. Percy. The Influence of Structure on Reactivity in Alkene Metathesis. 2014, 81-188. https://doi.org/10.1016/B978-0-12-800256-8.00002-3
    20. Allan Young, Mark A. Vincent, Ian H. Hillier, Jonathan M. Percy, Tell Tuttle. Forming a ruthenium isomerisation catalyst from Grubbs II: a DFT study. Dalton Trans. 2014, 43 (22) , 8493-8498. https://doi.org/10.1039/C4DT00464G
    21. Steven T. Diver, Jonathan M. French. Ruthenium Carbenes. 2013, 404-451. https://doi.org/10.1002/9781118730379.ch13
    22. James W. Herndon. The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2011. Coordination Chemistry Reviews 2013, 257 (21-22) , 2899-3003. https://doi.org/10.1016/j.ccr.2013.05.011
    23. Akio Saito, Yuji Hanzawa. Metathesis Reactions in Drug and Natural Product Synthesis. 2013, 1-46. https://doi.org/10.1002/9781118596784.ssd024
    24. Ian W. Ashworth, Ian H. Hillier, David J. Nelson, Jonathan M. Percy, Mark A. Vincent. Searching for the Hidden Hydrides: The Competition between Alkene Isomerization and Metathesis with Grubbs Catalysts. European Journal of Organic Chemistry 2012, 2012 (29) , 5673-5677. https://doi.org/10.1002/ejoc.201201036
    25. Joseph R. Clark, Steven T. Diver. ChemInform Abstract: Atom Economy in the Metathesis Cross‐Coupling of Alkenes and Alkynes.. ChemInform 2011, 42 (38) https://doi.org/10.1002/chin.201138045

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