Synthesis of rigid tetrahedral tetrafunctional molecules from 1,3,5,7-tetrakis(4-iodophenyl)adamantane

Mathias, Lon J.; Reichert, Veronica R.; Muir, Andrew V. G.

doi:10.1021/cm00025a002

Cited by 37 publications

(15 citation statements)

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“…The para-position of these phenyl rings can be easily iodinated or brominated in quantitative yields. 126 1,3,5,7-Tetrakis(4-iodophenyl)adamantane (275) and 1,3,5,7-tetrakis(4-ethynylphenyl)adamantane (276) have been used as key organic tectons to form self-assemblies. 99d Compounds 275 and 276 participate in a number of standard reactions including Pd-catalyzed Suzuki reactions, Sonogashira couplings, click reactions, and multicomponent cascade reactions.…”

Section: 357-tetrasubstituted Adamantanesmentioning

confidence: 99%

Synthetic Advances in the C–H Activation of Rigid Scaffold Molecules

Grover

Senge²

2020

Synthesis

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The remarkable structural and electronic properties of rigid non-conjugated hydrocarbons afford attractive opportunities to design molecular building blocks for both medicinal and material applications. The bridgehead positions provide the possibility to append diverse functional groups at specific angles and in specific orientations. The current review summarizes the synthetic development in CH functionalization of three rigid scaffolds namely: (a) cubane, (b) bicyclo[1.1.1]pentane (BCP), (c) adamantane.1 Introduction2 Cubane2.1 Cubane Synthesis2.2 Cubane Functionalization3 Bicyclo[1.1.1]pentane (BCP)3.1 BCP Synthesis3.2 BCP Functionalization4 Adamantane4.1 Adamantane Synthesis4.2 Adamantane Functionalization5 Conclusions and Outlook

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Section: 357-tetrasubstituted Adamantanesmentioning

confidence: 99%

Synthetic Advances in the C–H Activation of Rigid Scaffold Molecules

Grover

Senge²

2020

Synthesis

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“…In the presence of t-butylbromide (t-BuBr), IIa is prepared in 76% yield (Scheme 4). 49,50 The corresponding bromo (IIb) and iodo (IIc) derivatives are also readily to hand via electrophilic substitution (Scheme 4). 39 Gutiérrez has developed a synthetic approach towards 1,3,5,7-tetracyanoadamantane which gives in term access to the tetrakis(aminomethyl) and the tetrakiscarboxylates particularly interesting for the generation of coordination polymers.…”

Section: Syntheses Of Tetrakisphenylmethane I and Analoguesmentioning

confidence: 99%

Tetrahedral organic molecules as components in supramolecular architectures and in covalent assemblies, networks and polymers

Müller

Bräse

2014

RSC Adv.

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“…Phenyl groups provide a lateral extension of the 3D adamantane core and they can be easily halogenated to afford a range of functionalization possibilities. Para-substitution at the extremity of the four aryl groups is performed through iodination [72][73][74] or bromination [72,73] with high yields. 1,3,5,7-Tetrakis(4-iodophenyl)adamantane (13) can participate in numerous palladium catalyzed cross-coupling reactions including Suzuki-Miyaura [72,75,76], Sonogashira [29,36,73,75,77], Mizoroki-Heck [78], and multicomponent cascade reactions [27].…”

Section: Design Of Various Multi-functionalized Adamantane Building Bmentioning

confidence: 99%

Multifunctional adamantane derivatives as new scaffolds for the multipresentation of bioactive peptides

Grillaud

Bianco

2014

Journal of Peptide Science

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The remarkable structural and chemical properties of adamantane afford attractive opportunities to design various adamantane-based scaffolds for biomedical applications. A wide range of mono-functionalized adamantane compounds have already been investigated and reviewed, mostly as anti-viral agents. The four bridgehead positions of adamantane provide many possibilities to design poly-functional derivatives, and the recent conception of adamantane building blocks with multiple substituents has shown promising applications in several domains. In this review, we provide a detailed description of the different ways to synthesize multifunctional derivatives starting from adamantane molecule as the main core. We will then describe the interesting biological activity of the diverse multivalent scaffolds, focusing in particular on peptide-based systems. The results reported here will certainly encourage the development of novel adamantane-based structures for biological purposes.

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Synthesis of rigid tetrahedral tetrafunctional molecules from 1,3,5,7-tetrakis(4-iodophenyl)adamantane

Cited by 37 publications

References 0 publications

Synthetic Advances in the C–H Activation of Rigid Scaffold Molecules

Synthetic Advances in the C–H Activation of Rigid Scaffold Molecules

Tetrahedral organic molecules as components in supramolecular architectures and in covalent assemblies, networks and polymers

Multifunctional adamantane derivatives as new scaffolds for the multipresentation of bioactive peptides

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