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Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids.
Org Lett. 2007 Oct 11; 9(21):4227-30.OL

Abstract

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.

Authors+Show Affiliations

Tsukamoto 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 Y
No affiliation info available

MeSH

AlkynesBoronic AcidsCatalysisCombinatorial Chemistry TechniquesEstersIndenesMolecular StructureNaphtholsPalladium

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17867697

Citation

Tsukamoto, Hirokazu, and Yoshinori Kondo. "Palladium(II)-catalyzed Annulation of Alkynes With Ortho-ester-containing Phenylboronic Acids." Organic Letters, vol. 9, no. 21, 2007, pp. 4227-30.
Tsukamoto H, Kondo Y. Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids. Org Lett. 2007;9(21):4227-30.
Tsukamoto, H., & Kondo, Y. (2007). Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids. Organic Letters, 9(21), 4227-30.
Tsukamoto H, Kondo Y. Palladium(II)-catalyzed Annulation of Alkynes With Ortho-ester-containing Phenylboronic Acids. Org Lett. 2007 Oct 11;9(21):4227-30. PubMed PMID: 17867697.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids. AU - Tsukamoto,Hirokazu, AU - Kondo,Yoshinori, Y1 - 2007/09/15/ PY - 2007/9/18/pubmed PY - 2007/12/6/medline PY - 2007/9/18/entrez SP - 4227 EP - 30 JF - Organic letters JO - Org Lett VL - 9 IS - 21 N2 - 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. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17867697/Palladium_II__catalyzed_annulation_of_alkynes_with_ortho_ester_containing_phenylboronic_acids_ L2 - https://doi.org/10.1021/ol701776m DB - PRIME DP - Unbound Medicine ER -