TY - JOUR
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.
Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.
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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U2 - 10.1016/0022-328X(91)80026-G
DO - 10.1016/0022-328X(91)80026-G
M3 - Article
AN - SCOPUS:0001451770
VL - 409
SP - 411
EP - 420
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
SN - 0022-328X
IS - 3
ER -