Synthesis of helicenes and related compounds

螺烯及相关化合物的合成

• 批准号: 321658745
• 负责人: Professor Dr. Joachim Podlech
• 金额: --
• 依托单位: Institut für Organische Chemie (IOC)
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2016
• 资助国家: 德国
• 起止时间: 2015-12-31 至 2019-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/321658745?language=en
• 关键词: Synthesis; helicenes; related; compounds

Metal-catalyzed reactions of alpha-functionalized biphenyls with acetylenes and nitriles lead to phenanthrenes and nitriles, respectively. This well-known transformations shall be extended to functionalized acetylenes and nitriles to finally yield perylene quinones, benzo[de]anthracenes and benzoacridines. Starting with suitably substituted and thus chiral biphenyls would lead to enantiomerically pure, axially chiral perylene quinones. In expansion of this strategy, the reaction of oligo-ortho-phenylenes with acetylenes or nitriles would furnish helicenes and aza-helicenes, respectively. With this, the synthesis of substituted helicenes could be achieved. Since oligophenylenes are available in enantiomerically pure form, the enantioselective synthesis of helicenes is possible. Multiple Friedel-Crafts acylation of oligophenylenes with carboxyl chloride functions in the alpha positions would yield new helicene analogues with keto functions in the periphery, which could be further transformed and functionalized. Interesting physical properties can be expected for these compounds

α官能化的双苯基与乙酰基烯和硝酸盐的金属催化反应分别导致了3henthrenes和硝酸盐。这种众所周知的转化应扩展到功能化的乙酰基烯和硝酸盐，以最终产生perylene喹酮，苯并[de] anthracenes和苯二酰胺。从适当取代并因此，手性双苯基将导致对映体纯净的手性pery骨奎因酮。在扩大该策略的过程中，寡苯基苯乙烯与乙酰基烯或硝酸盐的反应分别提供螺旋烯和Aza-甲基烯。因此，可以实现取代的架的合成。由于寡素基因以映体纯形形式获得，因此可以对甲型素的对映选择性合成。在α位置，具有羧基氯化物功能的寡苯基苯乙烯的多种弗里德尔抗酶法将在外围产生新的Helicene类似物，并在外围产生酮功能，这可以进一步转化和官能化。这些化合物可以预期有趣的物理特性