Nickel-mediated cyclization of enynes under an atmosphere of carbon dioxide
Nickel-mediated cyclization of enynes under an atmosphere of carbon dioxide
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DOI：
10.1016/j.tet.2006.03.121
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发表时间：
2006-08-07
期刊：
影响因子：
2.1
通讯作者：
Sato, Yoshihiro
中科院分区：
文献类型：
--
作者：
Takimoto, Masanori;Mizuno, Takashi;Sato, Yoshihiro
研究了镍介导的α -欧米茄烯羧化反应。在化学计量量的零价镍配合物存在下，烯烃上具有吸电子基团的烯类通过分子内环化与二氧化碳反应，产率高的生成环羧酸。用这种羧基化方法制备了多种杂环化合物。该反应似乎是通过氧化环加成的α， ω -酶部分的零价镍配合物进行的。二氧化碳在Csp(3) -镍键上的区域选择性插入，以及由此产生的氧环中间体的水解。(c) 2006 Elsevier Ltd.版权所有。
Nickel-mediated carboxylation of alpha,omega-enyne was investigated. In the presence of a stoichiometric amount of zero-valent nickel complex, enynes having an electron-withdrawing group on alkene reacted with carbon dioxide via intramolecular cyclization to afford cvclic carboxylic acids in good yields. Various heterocyclic compounds were prepared by this carboxylative cyclization protocol. The reaction seems to proceed through oxidative cycloaddition of the alpha,omega-enyne moiety to a zero-valent nickel complex. regioselective insertion of carbon dioxide at the Csp(3) -nickel bond, and hydrolysis of the resulting oxanickelacycle intermediate. (c) 2006 Elsevier Ltd. All rights reserved.