Comparative activity of aryl, alkyl, and cycloalkyl halides in the suzuki reaction catalyzed with acyclic diaminocarbene complex of palladium

Comparative activity of aryl, alkyl, and cycloalkyl halides in the suzuki reaction catalyzed with acyclic diaminocarbene complex of palladium
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无环二氨基卡宾钯配合物催化的铃木反应中芳基、烷基和环烷基卤化物的活性比较

DOI:
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发表时间:
2015
影响因子:
0.9
通讯作者:
V. P. Boyarskii
V. P. Boyarskii
中科院分区:
化学4区
文献类型:
--
作者:
S. A. Kras’ko;S. S. Zlotskii;V. P. Boyarskii

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研究了卤代芳烃、烷烃和烷烃在非环二氨基卡宾钯配合物催化的Suzuki反应中的相对活性。在所有考察条件下,4-碘苯甲醚的活性均高于烷基卤化物。与4-甲基-1-(氯甲基)苯反应得到目标产物4-甲基-1-(苯甲基)苯以及大量的副产物;其他烷基和环烷基卤化物不参与交叉偶联反应。乙醇被认为是最适合该反应的溶剂。只有在聚乙二醇和水存在的情况下,乙腈中的反应才能提供显着的产物产率。
Relative activity of halogenated arenes, alkanes, and alkanes in the Suzuki reaction catalyzed with acyclic diaminocarbene complex of palladium has been investigated. Under all the investigated conditions, 4-iodoanisole has been more active than the alkyl halides. The reaction with 4-methyl-1-(chloromethyl)benzene has afforded the target 4-methyl-1-(phenylmethyl)benzene along with significant amount of by-products; other alkyl and cycloalkyl halides do not participate into the cross-coupling reaction. Ethanol has been found the most suitable solvent for the reaction. The reaction in acetonitrile provides noticeable yield of the products only in the presence of polyethylene glycol and water.
DOI: 10.1021/jo202686p
发表时间: 2012-03-16
期刊: The Journal of organic chemistry
影响因子: --
作者:
Colombel V;Rombouts F;Oehlrich D;Molander GA
通讯作者: Molander GA