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.
Morrill
Christie
C
Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Grubbs
Robert H
RH
D000475:Alkenes / Q000737:chemistry*; D000838:Anions; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007202:Indicators and Reagents; D008958:Models, Molecular; D012428:Ruthenium; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D000838:Anions; D001897:Boronic Acids; D007202:Indicators and Reagents; D014753:Vinyl Compounds; D012428:Ruthenium