Direct Carbon-Hydrogen Bond Functionalization of Heterocyclic Compounds
Direct Carbon-Hydrogen Bond Functionalization of Heterocyclic Compounds
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DOI：
10.1055/s-0030-1259332
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发表时间：
2011-02-01
期刊：
影响因子：
2
通讯作者：
Miura, Masahiro
中科院分区：
文献类型：
--
作者：
Hirano, Koji;Miura, Masahiro
本文综述了近年来杂环化合物的碳-氢键直接官能化反应，包括芳基化、烯基化、炔基化、烷基化和胺化反应。在芳基化和烯基化反应中，我们主要关注廉价的第一过渡元素的潜力，并展示了铜和镍催化剂的良好活性，这与传统的钯催化剂的活性相似。基于铜或镍的催化体系还能够与简单的末端炔以及炔基卤化物直接炔基化。另一方面，钯催化剂在相对困难的直接烷基化反应中的新应用。除了催化剂的开发之外，我们还引入了氯胺作为新型、高效的杂芳族碳氢键亲电胺化试剂;这些化合物可以简洁地合成在制药和药物化学中引起极大兴趣的氨基取代的唑类化合物。
This account summarizes our recent results on the direct carbon-hydrogen bond functionalization of heterocyclic compounds, including arylation, alkenylation, alkynylation, alkylation, and amination. In the arylation and alkenylation reactions, we mainly focus on the potential of less-expensive first transition elements and demonstrate the good activities of copper and nickel catalysts which are similar to those of conventional palladium ones. The catalytic systems based on copper or nickel also enable direct alkynylation with simple terminal alkynes, as well as with alkynyl halides. On the other hand, a new application of palladium catalysts in the relatively difficult direct alkylation is shown. In addition to the development of catalysts, we introduce chloramines as new, efficient electrophilic amination reagents for heteroaromatic carbon-hydrogen bonds; these compounds allow the concise synthesis of amino-substituted azoles that are of great interest in pharmaceutical and medicinal chemistry.