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Open AccessArticle

A Study of Palladium Catalyzed Intra/Intermolecular Cascade Cross Coupling/Cyclizations Involving Bicyclopropylidene

Department of Chemistry, Faculty of Arts &Science, Nigde University, Nigde 51240, Turkey
Molecules 2014, 19(5), 6058-6069; https://doi.org/10.3390/molecules19056058
Received: 13 February 2014 / Revised: 6 May 2014 / Accepted: 7 May 2014 / Published: 13 May 2014
(This article belongs to the Section Organic Chemistry)
The compounds [3-(2-Bromocyclohex-2-enyloxy)prop-1-ynyl]-tert-butyl-dimethylsilane 3, [4-(2-bromocyclohex-2-en-1-yloxy)but-2-yn-1-yloxy]tert-butyldimethylsilane 5 and dimethyl 2-(2-bromocyclohex-2-enyl)-2-(3-(tert-butyldimethylsilanyl)prop-2-ynyl)malonate 9 were prepared and subjected to palladium-catalyzed intra-intermolecular cascade cross couplings incorporating bicyclopropylidene 10 under two types of conditions. In the presence of Pd(OAc)2, PPh3 and K2CO3 in acetonitrile at 80 °C, the products were indene analogues, cross-conjugated tetraenes 11, 12 and 13, respectively. The corresponding spirocyclopropanated tricycle 16 in dimethylformamide at 110 °C was obtained, albeit in low yield (24%), and observed as an equimolar mixture of diastereomers, whereas 14, 15 were not fully isolated. View Full-Text
Keywords: cascade reactions; cross-coupling; palladium; cyclopropanes; electrocyclization cascade reactions; cross-coupling; palladium; cyclopropanes; electrocyclization
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Demircan, A. A Study of Palladium Catalyzed Intra/Intermolecular Cascade Cross Coupling/Cyclizations Involving Bicyclopropylidene. Molecules 2014, 19, 6058-6069.

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