Fourfold Suzuki-Miyaura and Sonogashira Cross-Coupling Reactions on Tetrahedral Methane and Adamantane Derivatives

An efficient way to generate a series of rigid tetrahedral organic building units from common methane and adamantane precursors is presented. Suzuki–Miyaura and Sonogashira cross‐coupling reactions are used to effectively generate these shape‐persistent molecular tectons. Especially theSonogashira r...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2011-03, Vol.2011 (9), p.1743-1754
Main Authors: Schilling, Christine I., Plietzsch, Oliver, Nieger, Martin, Muller, Thierry, Bräse, Stefan
Format: Article
Language:English
Subjects:
Adamantane
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Cross-coupling
Exact sciences and technology
Hydrocarbons
Molecular tecton
Noncondensed benzenic compounds
Organic building unit
Organic chemistry
Preparations and properties
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Summary:An efficient way to generate a series of rigid tetrahedral organic building units from common methane and adamantane precursors is presented. Suzuki–Miyaura and Sonogashira cross‐coupling reactions are used to effectively generate these shape‐persistent molecular tectons. Especially theSonogashira reactions employing the readily available tetrahedral alkynes and commercial iodides and bromides are very effective. Fourfold Suzuki–Miyaura and Sonogashira reactions on common tetrahedral methane and adamantane cores are presented leading to rigid organic building blocks for supramolecular networks.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201001567