Palladium-catalyzed enyne-yne [4 + 2] benzannulation as a new and general approach to polysubstituted benzenes

Vladimir Gevorgyan; Yoshinori Yamamoto

doi:10.1016/S0022-328X(98)01061-4

Palladium-catalyzed enyne-yne [4 + 2] benzannulation as a new and general approach to polysubstituted benzenes

Vladimir Gevorgyan, Yoshinori Yamamoto

Research output: Contribution to journal › Review article › peer-review

106 Scopus citations

Abstract

Monosubstituted conjugated enynes smoothly underwent [4 + 2] homodimerization in the presence of palladium catalyst to give 4, α- and 2,6-disubstituted styrenes. Analogous cross-cycloaddition of conjugated enynes and diynes afforded a variety of polysubstituted benzenes, including phenol and aniline derivatives. Alkynes and diynes in the presence of a palladium catalyst underwent novel formal [2 + 2 + 2] sequential cyclotrimerization to afford multifunctional benzenes in one step with high degrees of regio- and chemoselectivities. Mechanisms of these novel transformations are discussed.

Original language	English (US)
Pages (from-to)	232-247
Number of pages	16
Journal	Journal of Organometallic Chemistry
Volume	576
Issue number	1-2
DOIs	https://doi.org/10.1016/S0022-328X(98)01061-4
State	Published - Mar 15 1999
Externally published	Yes

Keywords

Alkynes
Benzene
Cycloaddition
Diynes
Enynes
Palladium

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0022-328X(98)01061-4

Cite this

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title = "Palladium-catalyzed enyne-yne [4 + 2] benzannulation as a new and general approach to polysubstituted benzenes",

abstract = "Monosubstituted conjugated enynes smoothly underwent [4 + 2] homodimerization in the presence of palladium catalyst to give 4, α- and 2,6-disubstituted styrenes. Analogous cross-cycloaddition of conjugated enynes and diynes afforded a variety of polysubstituted benzenes, including phenol and aniline derivatives. Alkynes and diynes in the presence of a palladium catalyst underwent novel formal [2 + 2 + 2] sequential cyclotrimerization to afford multifunctional benzenes in one step with high degrees of regio- and chemoselectivities. Mechanisms of these novel transformations are discussed.",

keywords = "Alkynes, Benzene, Cycloaddition, Diynes, Enynes, Palladium",

author = "Vladimir Gevorgyan and Yoshinori Yamamoto",

note = "Funding Information: Financial assistance of the Ministry of Education of Japan {\textquoteleft}Monbusho{\textquoteright} and the Ogasawara Foundation for the promotion of Science & Engineering is gratefully acknowledged. ",

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doi = "10.1016/S0022-328X(98)01061-4",

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T1 - Palladium-catalyzed enyne-yne [4 + 2] benzannulation as a new and general approach to polysubstituted benzenes

AU - Gevorgyan, Vladimir

AU - Yamamoto, Yoshinori

N1 - Funding Information: Financial assistance of the Ministry of Education of Japan ‘Monbusho’ and the Ogasawara Foundation for the promotion of Science & Engineering is gratefully acknowledged.

PY - 1999/3/15

Y1 - 1999/3/15

N2 - Monosubstituted conjugated enynes smoothly underwent [4 + 2] homodimerization in the presence of palladium catalyst to give 4, α- and 2,6-disubstituted styrenes. Analogous cross-cycloaddition of conjugated enynes and diynes afforded a variety of polysubstituted benzenes, including phenol and aniline derivatives. Alkynes and diynes in the presence of a palladium catalyst underwent novel formal [2 + 2 + 2] sequential cyclotrimerization to afford multifunctional benzenes in one step with high degrees of regio- and chemoselectivities. Mechanisms of these novel transformations are discussed.

AB - Monosubstituted conjugated enynes smoothly underwent [4 + 2] homodimerization in the presence of palladium catalyst to give 4, α- and 2,6-disubstituted styrenes. Analogous cross-cycloaddition of conjugated enynes and diynes afforded a variety of polysubstituted benzenes, including phenol and aniline derivatives. Alkynes and diynes in the presence of a palladium catalyst underwent novel formal [2 + 2 + 2] sequential cyclotrimerization to afford multifunctional benzenes in one step with high degrees of regio- and chemoselectivities. Mechanisms of these novel transformations are discussed.

KW - Alkynes

KW - Benzene

KW - Cycloaddition

KW - Diynes

KW - Enynes

KW - Palladium

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U2 - 10.1016/S0022-328X(98)01061-4

DO - 10.1016/S0022-328X(98)01061-4

M3 - Review article

AN - SCOPUS:0001752763

SN - 0022-328X

VL - 576

SP - 232

EP - 247

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 1-2

ER -

Palladium-catalyzed enyne-yne [4 + 2] benzannulation as a new and general approach to polysubstituted benzenes

Abstract

Keywords

ASJC Scopus subject areas

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