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Published July 25, 2003 | Supplemental Material
Journal Article Open

Synthesis of Functionalized Vinyl Boronates via Ruthenium-Catalyzed Olefin Cross-Metathesis and Subsequent Conversion to Vinyl Halides


Functionalized vinyl pinacol boronates suitable for Suzuki cross-coupling reactions are synthesized using ruthenium-catalyzed olefin cross-metathesis of 1-propenyl pinacol boronate and various alkenes, including functionalized and 1,1-disubstituted alkenes. The resultant boronate cross products are stereoselectively transformed into predominantly Z-vinyl bromides and E-vinyl iodides. The vinyl bromides may be synthesized in a two-step, one-pot synthesis from a variety of olefins, resulting in a Z-selective formal vinyl bromide cross-metathesis reaction.

Additional Information

© 2003 American Chemical Society. Received 25 April 2003. Published online 26 June 2003. Published in print 1 July 2003. We thank the National Institutes of Health for financial support and Brian J. Kwan for synthesizing compounds 18 and 20. We also thank Daniel P. Sanders, Dr. Steven D. Goldberg, Dr. Brian T. Connell, Dr. Arnab K. Chatterjee, and Dr. Jennifer A. Love for helpful suggestions and insight.

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Supplemental Material - jo0345345si20030425_073609.pdf

Supplemental Material - jo0345345si20030429_030216.pdf


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