Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids

Hirokazu Tsukamoto; Yoshinori Kondo

doi:10.1021/ol701776m

Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids

Hirokazu Tsukamoto, Yoshinori Kondo

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

81 Citations (Scopus)

Abstract

Palladlum(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.

Original language	English
Pages (from-to)	4227-4230
Number of pages	4
Journal	Organic letters
Volume	9
Issue number	21
DOIs	https://doi.org/10.1021/ol701776m
Publication status	Published - 2007 Oct 11

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids",

abstract = "Palladlum(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.",

author = "Hirokazu Tsukamoto and Yoshinori Kondo",

year = "2007",

month = oct,

day = "11",

doi = "10.1021/ol701776m",

language = "English",

volume = "9",

pages = "4227--4230",

journal = "Organic Letters",

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T1 - Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids

AU - Tsukamoto, Hirokazu

AU - Kondo, Yoshinori

PY - 2007/10/11

Y1 - 2007/10/11

N2 - Palladlum(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.

AB - Palladlum(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.

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U2 - 10.1021/ol701776m

DO - 10.1021/ol701776m

M3 - Article

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 21

ER -

Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids

Abstract

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