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Molecules 2014, 19(5), 6058-6069; doi:10.3390/molecules19056058
Article

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

Received: 13 February 2014; in revised form: 6 May 2014 / Accepted: 7 May 2014 / Published: 13 May 2014
(This article belongs to the Section Organic Synthesis)
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Abstract: 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.
Keywords: cascade reactions; cross-coupling; palladium; cyclopropanes; electrocyclization cascade reactions; cross-coupling; palladium; cyclopropanes; electrocyclization
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Demircan, A. A Study of Palladium Catalyzed Intra/Intermolecular Cascade Cross Coupling/Cyclizations Involving Bicyclopropylidene. Molecules 2014, 19, 6058-6069.

AMA Style

Demircan A. A Study of Palladium Catalyzed Intra/Intermolecular Cascade Cross Coupling/Cyclizations Involving Bicyclopropylidene. Molecules. 2014; 19(5):6058-6069.

Chicago/Turabian Style

Demircan, Aydin. 2014. "A Study of Palladium Catalyzed Intra/Intermolecular Cascade Cross Coupling/Cyclizations Involving Bicyclopropylidene." Molecules 19, no. 5: 6058-6069.


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