Palladium-catalyzed reactions of vinyl bromides with disubstituted alkynes: a new synthesis of fulvenes

Lee J. Silverberg; Guangzhong Wu; Arnold L. Rheingold; Richard F. Heck

doi:10.1016/0022-328X(91)80026-G

Palladium-catalyzed reactions of vinyl bromides with disubstituted alkynes: a new synthesis of fulvenes

Lee J. Silverberg, Guangzhong Wu, Arnold L. Rheingold, Richard F. Heck

Penn State Schuylkill

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

37 Scopus citations

Abstract

The palladium-catalyzed reaction of vinylic bromides with disubstituted acetylenes at 100°C in the presence of triethylamine produces penta- or hexa-substituted fulvenes in low to moderate yields. Reactions with 3-hexyne under the same conditions usually yield dialkylidenecyclopentenes as products, apparently by rearrangement of the expected fulvenes. Fulvenes formed from the reaction of disubstituted alkynes with Z-2-bromovinyl ethyl ether can be hydrolyzed to produce cyclopentadiene carboxaldehydes.

Original language	English (US)
Pages (from-to)	411-420
Number of pages	10
Journal	Journal of Organometallic Chemistry
Volume	409
Issue number	3
DOIs	https://doi.org/10.1016/0022-328X(91)80026-G
State	Published - Jun 4 1991

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/0022-328X(91)80026-G

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title = "Palladium-catalyzed reactions of vinyl bromides with disubstituted alkynes: a new synthesis of fulvenes",

abstract = "The palladium-catalyzed reaction of vinylic bromides with disubstituted acetylenes at 100°C in the presence of triethylamine produces penta- or hexa-substituted fulvenes in low to moderate yields. Reactions with 3-hexyne under the same conditions usually yield dialkylidenecyclopentenes as products, apparently by rearrangement of the expected fulvenes. Fulvenes formed from the reaction of disubstituted alkynes with Z-2-bromovinyl ethyl ether can be hydrolyzed to produce cyclopentadiene carboxaldehydes.",

author = "Silverberg, \{Lee J.\} and Guangzhong Wu and Rheingold, \{Arnold L.\} and Heck, \{Richard F.\}",

note = "Funding Information: Additional support was provided by the Center for Catalytic Science and Technology of the University of Delaware. We thank Johnson Matthey, Inc. for the loan of the palladium chloride used in this study. Funding Information: Acknowledgment is made to the Donors of the Petroleum Research Fund, administered by the American Chemical Society, for partial support of this research.",

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doi = "10.1016/0022-328X(91)80026-G",

language = "English (US)",

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pages = "411--420",

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T1 - Palladium-catalyzed reactions of vinyl bromides with disubstituted alkynes

T2 - a new synthesis of fulvenes

AU - Silverberg, Lee J.

AU - Wu, Guangzhong

AU - Rheingold, Arnold L.

AU - Heck, Richard F.

N1 - Funding Information: Additional support was provided by the Center for Catalytic Science and Technology of the University of Delaware. We thank Johnson Matthey, Inc. for the loan of the palladium chloride used in this study. Funding Information: Acknowledgment is made to the Donors of the Petroleum Research Fund, administered by the American Chemical Society, for partial support of this research.

PY - 1991/6/4

Y1 - 1991/6/4

N2 - The palladium-catalyzed reaction of vinylic bromides with disubstituted acetylenes at 100°C in the presence of triethylamine produces penta- or hexa-substituted fulvenes in low to moderate yields. Reactions with 3-hexyne under the same conditions usually yield dialkylidenecyclopentenes as products, apparently by rearrangement of the expected fulvenes. Fulvenes formed from the reaction of disubstituted alkynes with Z-2-bromovinyl ethyl ether can be hydrolyzed to produce cyclopentadiene carboxaldehydes.

AB - The palladium-catalyzed reaction of vinylic bromides with disubstituted acetylenes at 100°C in the presence of triethylamine produces penta- or hexa-substituted fulvenes in low to moderate yields. Reactions with 3-hexyne under the same conditions usually yield dialkylidenecyclopentenes as products, apparently by rearrangement of the expected fulvenes. Fulvenes formed from the reaction of disubstituted alkynes with Z-2-bromovinyl ethyl ether can be hydrolyzed to produce cyclopentadiene carboxaldehydes.

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JF - Journal of Organometallic Chemistry

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ER -

Palladium-catalyzed reactions of vinyl bromides with disubstituted alkynes: a new synthesis of fulvenes

Abstract

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