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Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis

Ming Joo Koh, Thach T. Nguyen, Hanmo Zhang, Richard R. Schrock and Amir H. Hoveyda*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email:

M. J. Koh, T. T. Ngyuen, H. Zhang, R. R. Schrock, A. H. Hoveyda, Nature, 2016, 531, 459-465.

DOI: 10.1038/nature17396

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Previously unknown halo-substituted molybdenum alkylidene species are exceptionally reactive and are able to participate in high-yielding olefin metathesis reactions that afford acyclic 1,2-disubstituted Z-alkenyl halides. Transformations are promoted by small amounts of a catalyst that is generated in situ and used with unpurified, commercially available and easy-to-handle liquid 1,2-dihaloethene reagents.

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Reactions function similarly well in toluene from our experiments, benzene was just used as a customary practice.

Ming Joo Koh, April 4, 2016

Key Words

cross metathesis, alkenyl halides, alkenyl chlorides, alkenyl fluorides

ID: J54-Y2015