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Synthesis of functionalized vinyl boronates via ruthenium-catalyzed olefin cross-metathesis and subsequent conversion to vinyl halides.
J Org Chem. 2003 Jul 25; 68(15):6031-4.JO

Abstract

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.

Authors+Show Affiliations

Morrill C
Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Grubbs RH
No affiliation info available

MeSH

AlkenesAnionsBoronic AcidsCatalysisIndicators and ReagentsModels, MolecularRutheniumVinyl Compounds

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

12868943

Citation

Morrill, Christie, and Robert H. Grubbs. "Synthesis of Functionalized Vinyl Boronates Via Ruthenium-catalyzed Olefin Cross-metathesis and Subsequent Conversion to Vinyl Halides." The Journal of Organic Chemistry, vol. 68, no. 15, 2003, pp. 6031-4.
Morrill C, Grubbs RH. Synthesis of functionalized vinyl boronates via ruthenium-catalyzed olefin cross-metathesis and subsequent conversion to vinyl halides. J Org Chem. 2003;68(15):6031-4.
Morrill, C., & Grubbs, R. H. (2003). Synthesis of functionalized vinyl boronates via ruthenium-catalyzed olefin cross-metathesis and subsequent conversion to vinyl halides. The Journal of Organic Chemistry, 68(15), 6031-4.
Morrill C, Grubbs RH. Synthesis of Functionalized Vinyl Boronates Via Ruthenium-catalyzed Olefin Cross-metathesis and Subsequent Conversion to Vinyl Halides. J Org Chem. 2003 Jul 25;68(15):6031-4. PubMed PMID: 12868943.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of functionalized vinyl boronates via ruthenium-catalyzed olefin cross-metathesis and subsequent conversion to vinyl halides. AU - Morrill,Christie, AU - Grubbs,Robert H, PY - 2003/7/19/pubmed PY - 2004/3/9/medline PY - 2003/7/19/entrez SP - 6031 EP - 4 JF - The Journal of organic chemistry JO - J Org Chem VL - 68 IS - 15 N2 - 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. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/12868943/Synthesis_of_functionalized_vinyl_boronates_via_ruthenium_catalyzed_olefin_cross_metathesis_and_subsequent_conversion_to_vinyl_halides_ DB - PRIME DP - Unbound Medicine ER -