过渡金属催化的多炔基化合物高选择性亲电环异构化反应研究

doi:10.6023/cjoc201412056

摘要/Abstract

对我们研究小组近几年来在过渡金属催化的复合炔基化合物的高选择性环异构化反应方面取得的成果进行了小结. 通过底物与亲电试剂的分子间串联亲电环化反应, 有效地构建了官能团化的苯并[a]芴醇和密集三取代的卤代炔基萘酮环结构单元衍生物. 基于此研究基础, 又发展了一类过渡金属催化的1,6-二炔醇酯或1,5-二炔类化合物的分子内环异构化反应, 构建了官能团化的亚甲基茚结构单元以及含三氟甲硫基结构的茚衍生物. 此外对影响反应的可能因素也做了讨论, 提出了可能的反应机理.

关键词: 过渡金属催化, 多炔基化合物, 环异构化, 串联反应

This article summarized our recent progress in transition-metal-catalyzed highly selective cycloisomerization reactions of 1,5- and/or 1,6-diylol compounds, which selectively provided useful access to polyfunctionalized benzo[a]fluorenol and densely trisubstituted naphthalene derivatives. Based on these results, we have also developed transition-metal-catalyzed tandem cycloisomerization reactions of 1,6-diynl esters or 1,5-diyls, affording a series of methelene benzofulvenes derivatives and trifluoromethanesulfanyl benzofulvenes in chemo- and regio-selective manner. In addition, the factors that may affect the reaction processes were studied, and the possible reaction mechanisms are proposed.

Key words: transition-metal-catalyzed, multi-alkynyl compounds, cycloisomerization, tandem reaction

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朱辉, 严冰玉, 曹杨, 陈知远. 过渡金属催化的多炔基化合物高选择性亲电环异构化反应研究[J]. 有机化学, 2015, 35(3): 509-521.

Zhu Hui, Yan Bingyu, Cao Yang, Chen Zhiyuan. Transition-Metal-Catalyzed Highly Selective Electrophilic Cycloisomerization Reaction of Multi-alkynyl Compounds[J]. Chin. J. Org. Chem., 2015, 35(3): 509-521.

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