Ruthenium-catalyzed carbon-carbon bond formation via the cleavage of an unreactive aryl carbon-nitrogen bond in aniline derivatives with organoboronates
Ruthenium-catalyzed carbon-carbon bond formation via the cleavage of an unreactive aryl carbon-nitrogen bond in aniline derivatives with organoboronates
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DOI：
10.1021/ja0713431
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发表时间：
2007-05-16
影响因子：
15
通讯作者：
Kakiuchi, Fumitoshi
中科院分区：
文献类型：
--
作者：
Ueno, Satoshi;Chatani, Naoto;Kakiuchi, Fumitoshi
RuH_2(CO)(PPh_3)(3)催化2-氨基-6-甲基苯乙酮与苯基硼酸2，2-二甲基-1，3-丙二醇酯在回流甲苯中的反应，通过芳基碳氮键断裂，以83%的产率得到相应的苯基化产物。该反应涉及两个显著的特征：(1)偶联是通过苯胺中的芳基碳-氮键与Ru络合物的氧化加成进行的；(2)C-C键的形成是通过Ru-NR2物种与有机硼化合物之间的易位反应进行的。
The RuH2(CO)(PPh3)(3)-catalyzed reaction of 2-amino-6-methylacetophenone with phenylboronic acid 2,2-dimethyl-1,3-propanediol ester in refluxing toluene gave the corresponding phenylation product in 83% yield via aryl carbon-nitrogen bond cleavage. This reaction involves two notable features: (1) the coupling proceeds via the oxidative addition of an aryl carbon-nitrogen bond in anilines to the ruthenium complex, and (2) C-C bond formation takes place via transmetalation between the Ru-NR2 species and organoboronates.