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New Efficient Multicomponent Reactions with C-C Coupling for Combinatorial Application in Liquid and on Solid Phase.

de Meijere A¹, Nüske, Es-Sayed

¹Institute für Organische und Anorganische Chemie der Universität, D-37077 Göttingen (Germany).

Angewandte Chemie (International Ed. in English)

|January 29, 2000

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The First Stable Diazonium Ion on Solid Support-Investigations on Stability and Usage as Linker and Scavenger in Solid-Phase Organic Synthesis Nitrogen-Based Linkers, Part 8. This work was supported by the Fonds der Chemischen Industrie (Liebig-Stipend to S.B.) and the Deutsche Forschungsgemeinschaft (BR1750-1). We thank Prof. Dr. D. Enders for the generous support of our work. The companies BASF AG, Bayer AG, Degussa-Hüls AG, and Calbiochem-Novabiochem AG are acknowledged for donations of chemicals and Grünenthal GmbH for financial support. For DSC measurements we also thank Prof. Dr. Franz-Josef Wortmann and Dr. Numan Özgün at the Deutsches Wollforschungsinstitut (DWI) at the RWTH Aachen. Part 7: M. Lormann, S. Dahmen, S. Bräse, Tetrahedron Lett. 2000, 41, 3813-3816.

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Mono-, di-, and trimetallic complexes of the nonalternating polycondensed pi-perimeter decacyclene, C36H18: synthesis, structure, and spectroelectrochemistry of

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This study demonstrates a novel method for creating complex molecules by forming up to nine carbon-carbon bonds from multiple starting materials. Solid-phase synthesis unexpectedly outperformed liquid-phase methods in this selective bond-forming reaction.

Area of Science:

Organic Chemistry
Synthetic Chemistry
Catalysis

Background:

Efficiently constructing complex organic molecules with multiple carbon-carbon bonds is a significant challenge in synthetic chemistry.
Developing selective and high-yielding reactions is crucial for synthesizing novel compounds and materials.

Purpose of the Study:

To develop a novel synthetic strategy for the selective formation of multiple carbon-carbon bonds.
To compare the efficacy of liquid-phase versus solid-phase synthesis for this multi-component reaction.
To explore the scope and limitations of this new bond-forming methodology.

Main Methods:

A multi-component reaction involving an alkene, a haloarene, and a dienophile was designed.
The reaction was performed under both liquid-phase and solid-phase conditions.

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The selectivity and yield of carbon-carbon bond formation were analyzed.

Main Results:

Up to nine selective carbon-carbon bonds were formed from up to seven distinct components.
The solid-phase reaction demonstrated a surprising superiority over the liquid-phase approach.
The reaction pathway allows for the construction of complex molecular architectures.

Conclusions:

A versatile and selective method for synthesizing complex molecules has been established.
Solid-phase synthesis offers significant advantages for this specific multi-component reaction, potentially due to improved reactant proximity and simplified purification.
This work provides a new tool for organic chemists aiming to build intricate molecular structures efficiently.