Synthesis of <i>o</i> ‐Bis(3‐indolyl)arenes under Br?nsted Acid Catalysis: Carbonyl Compounds as Sources of Aryl Groups
Synthesis of <i>o</i> ‐Bis(3‐indolyl)arenes under Br?nsted Acid Catalysis: Carbonyl Compounds as Sources of Aryl Groups
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布朗斯台德酸催化下合成<i>o</i>-双(3-吲哚基)芳烃：羰基化合物作为芳基的来源
DOI：
10.1002/adsc.202201340
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发表时间：
2023
期刊：
影响因子：
--
通讯作者：
Tsuchimoto Teruhisa
中科院分区：
文献类型：
--
作者：
Tokunaga Rei;Okusa Takumi;Tsuchimoto Teruhisa
开发了一种通过使吲哚与7-氧杂双环[2.2.1]庚-5-烯-2-酮及其不具有芳环的衍生物反应来合成偶氮-双（3-吲哚基）芳烃的方法。所有23个未知的双（3-吲哚基）芳烃可以使用该方法获得。钯催化可用于扩大邻-双（3-吲哚基）芳烃的π-共轭面积，提供芳基-、炔基-和烯基-单元-安装的-双（3-吲哚基）芳烃和苯并[c]吲哚并[2，3-a]咔唑，其衍生化可有效提高荧光量子产率。一个可能的反应机理提出了几个机制研究的基础上。
A method of synthesizingo‐bis(3‐indolyl)arenes was developed by reacting indoles with 7‐oxabicyclo[2.2.1]hept‐5‐en‐2‐one and derivatives thereof having no aromatic ring. All 23 unknowno‐bis(3‐indolyl)arenes could be obtained using this method. Palladium catalysis is useful for enlarging the π‐conjugated area ofo‐bis(3‐indolyl)arenes, delivering aryl‐, alkynyl‐, and alkenyl‐unit‐installedo‐bis(3‐indolyl)arenes, and benzo[c]indolo[2,3‐a]carbazoles, the derivatization to which is effective for raising fluorescence quantum yield. A possible reaction mechanism is proposed based on several mechanistic studies.