Studies on Carbon-Carbon Bond Forming Reactions Utilizing Activation of Unsaturated Hydrocarbons and Heteroaromatic Compounds by Metal Sulfonate Catalysts
Studies on Carbon-Carbon Bond Forming Reactions Utilizing Activation of Unsaturated Hydrocarbons and Heteroaromatic Compounds by Metal Sulfonate Catalysts
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金属磺酸盐催化剂活化不饱和烃和杂芳族化合物的碳-碳键形成反应研究
DOI：
10.5059/yukigoseikyokaishi.64.752
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发表时间：
2006
影响因子：
0.2
通讯作者：
T. Tsuchimoto
中科院分区：
文献类型：
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作者：
T. Tsuchimoto
迄今为止，刘易斯酸已被用作介体或催化剂，主要用于活化含杂原子的化合物，如羰基化合物、亚胺和烷基卤化物。相比之下，我们一直专注于开发利用金属磺酸盐催化剂活化烃的新的碳-碳键形成反应。在这种情况下，我们发现，芳烃以及杂环芳烃加成到炔在三氟甲磺酸铟[In（OTf）3，Tf= SO2 CF 3]作为催化剂的存在下。这些发现之后，芳基和杂芳基环化[a]咔唑的简便合成的发展炔丙基醚与2-芳基和2-杂芳基吲哚的反应。除了上述反应之外，金属三氟甲磺酸盐在钯催化剂的帮助下催化乙烯基芳烃的二聚（C = C的活化）、使用吡咯基作为碳离去基团的亲核取代（C-C的活化）和内酰胺与杂环芳烃之间的氧化偶联（C-H的活化）。
Lewis acids have been used as a mediator or a catalyst so far mainly for activation of heteroatom-containing compounds like carbonyl compounds, imines and alkyl halides. In contrast, we have been focusing on developing new carbon-carbon bond forming reactions utilizing activation of hydrocarbons by a metal sulfonate catalyst. In this context, we found that arenes as well as heterocyclic arenes add to alkynes in the presence of indium triflate [In (OTf)3, Tf=SO2CF3] as a catalyst. These findings are followed by development of facile synthesis of aryl-and heteroarylannulated [a] carbazoles by the reaction of propargyl ethers with 2-aryl-and 2-heteroarylindoles. In addition to the above reactions, metal triflates catalyzed dimerization of vinylarenes with the aid of a palladium catalyst (activation of C = C), nucleophilic substitution using a pyrrolyl group as a carbon leaving group (activation of C-C) and oxidative coupling between lactams and heterocyclic arenes (activation of C-H).