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JoVE Journal
Chemistry
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Func...
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Func...
JoVE Journal
Chemistry
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JoVE Journal Chemistry
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Full Text
17,743 Views
12:07 min
April 1, 2013

DOI: 10.3791/50511-v

Laura S. Kocsis1, Erica Benedetti1, Kay M. Brummond1

1Department of Chemistry,University of Pittsburgh

Microwave-assisted intramolecular dehydrogenative Diels-Alder (DA) reactions provide concise access to functionalized cyclopenta[b]naphthalene building blocks. The utility of this methodology is demonstrated by one-step conversion of the dehydrogenative DA cycloadducts into novel solvatochromic fluorescent dyes via Buchwald-Hartwig palladium-catalyzed cross-coupling reactions.

The overall goal of the following experiment is to generate functionalized napoles via a microwave assisted dehydrogenate dehydro ideals alder or DDDA reaction. This is achieved by microwave irradiation of styre precursors to produce diverse lene substrates. As a second step, a buckwald hardwig palladium catalyzed cross coupling reaction of the hynes with an amine is conducted.

This results in naphthalene containing electron donating and electron withdrawing groups that function as slv chromic fluorescent dyes, and are structurally related to a commercially available dye pro. Dan next solutions of the dye are prepared in order to measure the selected photo physical properties of the new substrates. This novel synthetic approach affords access to molecular architectures, possessing desirable photo, physical properties, and attractive chemical properties.

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Microwave-assistedIntramolecular Dehydrogenative Diels-Alder ReactionsFunctionalized NaphthalenesSolvatochromic DyesCyclopenta[b]naphthalenesBuchwald-Hartwig Palladium-catalyzed Cross-couplingFluorescence Spectroscopy

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