Palladium(0)-catalyzed direct cross-coupling reaction of allylic alcohols with aryl- and alkenylboronic acids.
Allylic alcohols can be used directly for the palladium(0)-catalyzed allylation of aryl- and alkenylboronic acids with a wide variety of functional groups. A triphenylphosphine-ligated palladium catalyst turns out to be most effective for the cross-coupling reaction and its low loading (less than 1 mol%) leads to formation of the coupling product in high yield. The Lewis acidity of the organoboron reagents and poor leaving ability (high basicity) of the hydroxyl group are essential for the cross-coupling reaction. The reaction process is atom-economical and environmentally benign, because it needs neither preparation of allyl halides and esters nor addition of stoichiometric amounts of a base. Furthermore, allylic alcohols containing another unsaturated carbon-carbon bond undergo arylative cyclization reactions leading to cyclopentane formation.
Tsukamoto
Hirokazu
H
Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki-aza aoba 6-3, Aoba-ku, Sendai 980-8578, Japan. hirokazu@mail.pharm.tohoku.ac.jp
Uchiyama
Tomomi
T
Suzuki
Takamichi
T
Kondo
Yoshinori
Y
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis; D008024:Ligands; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
D001897:Boronic Acids; D003517:Cyclopentanes; D008024:Ligands; D020005:Propanols; D012997:Solvents; C006463:allyl alcohol; D010165:Palladium