Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids.
Palladium(II) catalyzes annulation of internal alkynes with methyl 2-boronobenzoate and (2-boronophenyl)acetate to provide 2,3-disubstituted indenones and 3,4-disubstituted 2-naphthols, respectively. The annulation reaction would proceed through transmetalation of Pd(II) with the boron reagents and insertion of the alkynes, followed by unprecedented 1,2-addition of the generated alkenylpalladium(II) species to the intramolecular ester group.
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
Kondo
Yoshinori
Y
D000480:Alkynes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*
D000480:Alkynes; D001897:Boronic Acids; D004952:Esters; D007192:Indenes; D009284:Naphthols; D010165:Palladium; C010686:benzeneboronic acid