Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles
Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles
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DOI：
10.1021/jo060308u
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发表时间：
2006-05-26
影响因子：
3.6
通讯作者：
Nishida, Atsushi
中科院分区：
文献类型：
--
作者：
Arisawa, Mitsuhiro;Terada, Yukiyoshi;Nishida, Atsushi
利用第二代Grubbs钌催化剂与乙烯氧基三甲基硅烷反应，合成了一种含氮杂环卡宾（NHC）配体的钌氢化物配合物。该钌氢化物配合物对末端烯烃的选择性异构化和1，6-二烯的环化异构化反应具有很高的催化活性。N-烯丙基-邻乙烯基苯胺的这些反应为吲哚和3-亚甲基-2，3-二氢吲哚等杂环化合物的合成提供了新的方法，这些杂环化合物是具有生物活性的天然产物的重要配体。这些程序解决了面向多样性的合成中的一个重要问题。
A pure ruthenium hydride complex with N-heterocyclic carbene (NHC) ligand was efficiently generated from the reaction of a second-generation Grubbs ruthenium catalyst with vinyloxytrimethylsilane and unambiguously characterized. This ruthenium hydride complex showed high catalytic activity for the selective isomerization of terminal olefin and for the cycloisomerization of 1,6-dienes. These reactions of N-allyl-o-vinylaniline lead to novel synthetic methods for heterocycles such as indoles and 3-methylene-2,3-dihydroindoles, which are useful synthons for bioactive natural products. These procedures address an important issue in diversity-oriented synthesis.