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Keywords = nonaflate

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9 pages, 1399 KB  
Article
Synthesis of a Bcl9 Alpha-Helix Mimetic for Inhibition of PPIs by a Combination of Electrooxidative Phenol Coupling and Pd-Catalyzed Cross Coupling
by Martin Vareka, Benedikt Dahms, Mario Lang, Minh Hao Hoang, Melanie Trobe, Hansjörg Weber, Maximilian M. Hielscher, Siegfried R. Waldvogel and Rolf Breinbauer
Catalysts 2020, 10(3), 340; https://doi.org/10.3390/catal10030340 - 19 Mar 2020
Cited by 8 | Viewed by 5225
Abstract
Teraryl-based alpha-helix mimetics have resulted in efficient inhibitors of protein-protein interactions (PPIs). Extending the concept to even longer oligoarene systems would allow for the mimicking of even larger interaction sites. We present a highly efficient synthetic modular access to quateraryl alpha-helix mimetics, in [...] Read more.
Teraryl-based alpha-helix mimetics have resulted in efficient inhibitors of protein-protein interactions (PPIs). Extending the concept to even longer oligoarene systems would allow for the mimicking of even larger interaction sites. We present a highly efficient synthetic modular access to quateraryl alpha-helix mimetics, in which, at first, two phenols undergo electrooxidative dehydrogenative cross-coupling. The resulting 4,4′-biphenol is then activated by conversion to nonaflates, which serve as leaving groups for iterative Pd-catalyzed Suzuki-cross-coupling reactions with suitably substituted pyridine boronic acids. This work, for the first time, demonstrates the synthetic efficiency of using both electroorganic as well as transition-metal catalyzed cross-coupling in the assembly of oligoarene structures. Full article
(This article belongs to the Special Issue Transition Metal Catalyzed Cross-Coupling Reactions)
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13 pages, 447 KB  
Article
Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic Acid
by Miyuki Yamaguchi, Takeshi Kimura, Naomi Shinohara and Kei Manabe
Molecules 2013, 18(12), 15207-15219; https://doi.org/10.3390/molecules181215207 - 10 Dec 2013
Cited by 5 | Viewed by 6137
Abstract
A repetitive two-step method involving the Pd-catalyzed Suzuki-Miyaura coupling of hydroxyterphenylboronic acid and the subsequent nonaflation of the hydroxy group has been developed for the synthesis of oligophenylenes. This method readily afforded o,o,p- and o,p-oligophenylenes [...] Read more.
A repetitive two-step method involving the Pd-catalyzed Suzuki-Miyaura coupling of hydroxyterphenylboronic acid and the subsequent nonaflation of the hydroxy group has been developed for the synthesis of oligophenylenes. This method readily afforded o,o,p- and o,p-oligophenylenes with defined chain lengths. X-ray crystallography was employed to obtain the structure of the o,p-oligophenylene 9-mer. Full article
(This article belongs to the Special Issue Palladium Catalysts)
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