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

Schilling, Christine I.; Plietzsch, Oliver; Nieger, Martin; Müller, Thierry; Bräse, Stefan

doi:10.1002/ejoc.201001567

Cited by 30 publications

(13 citation statements)

References 60 publications

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“…In a second step, those triiodobenzenes were subjected to a three-fold Sonogashira coupling procedure with the corresponding 4-ethynylbenzoates (Scheme 1). [19] C 3 -Symmetric, highly conjugated π-systems were obtained with electronically matching donor and acceptor substitution at the central benzene core and the phenylethynyl periphery, respectively. This substitution pattern, that is, the resulting electronic distribution, promotes the intramolecular stacking interactions and directs the supramolecular order in the bulk.…”

Section: Resultsmentioning

confidence: 99%

Controlling the Macroscopic Chirality of Organic Materials Based on 1,3,5‐Trialkynylbenzenes

et al. 2012

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Section: Resultsmentioning

confidence: 99%

Controlling the Macroscopic Chirality of Organic Materials Based on 1,3,5‐Trialkynylbenzenes

et al. 2012

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“…These encompass adamantanes with aryl arms of different size and structure, including adamantanes with dialkoxyphenyl arms (1 and 2) and 1,3,5,7-tetrakis(p-hydroxybiphenyl) adamantane (TBA, 3) with longer arms and terminal alcohol groups. The TAAs were prepared using known methods (Alexandre et al 2017;Schwenger et al 2015;Schilling et al 2011;Singh et al 2012), and were subjected to thermal crystallization to study their suitability for gas uptake.…”

Section: Single-crystals Of Hostsmentioning

confidence: 99%

Non-porous organic crystals and their interaction with guest molecules from the gas phase

et al. 2020

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Some organic molecules encapsulate solvents upon crystallization. One class of compounds that shows a high propensity to form such crystalline solvates are tetraaryladamantanes (TAAs). Recently, tetrakis(dialkoxyphenyl)-adamantanes have been shown to encapsulate a wide range of guest molecules in their crystals, and to stabilize the guest molecules against undesired reactions. The term ‘encapsulating organic crystals’ (EnOCs) has been coined for these species. In this work, we studied the behavior of three TAAs upon exposition to different guest molecules by means of sorption technique. We firstly measured the vapor adsorption/desorption isotherms with water, tetrahydrofuran and toluene, and secondly, we studied the uptake of methane on dry and wet TAAs. Uptake of methane beyond one molar equivalent was detected for wet crystals, even though the materials showed a lack of porosity. Thus far, such behavior, which we ascribe to methane hydrate formation, had been described for porous non-crystalline materials or crystals with detectable porosity, not for non-porous organic crystals. Our results show that TAA crystals have interesting properties beyond the formation of conventional solvates. Gas-containing organic crystals may find application as reservoirs for gases that are difficult to encapsulate or are slow to form crystalline hydrates in the absence of a host compound. Wet tetraaryladamantane crystals take up methane in form of methane hydrate structure I, even though they appear non-porous to argon.

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“…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]. The preparation of 'clickable' building blocks from the tetraiodine derivative offers potential design of various adamantane scaffolds (Scheme 1).…”

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

Cited by 30 publications

References 60 publications

Controlling the Macroscopic Chirality of Organic Materials Based on 1,3,5‐Trialkynylbenzenes

Controlling the Macroscopic Chirality of Organic Materials Based on 1,3,5‐Trialkynylbenzenes

Non-porous organic crystals and their interaction with guest molecules from the gas phase

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

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