Silver Oxide as a Novel Catalyst for Carbon-Carbon Bond-forming Reactions in Aqueous Media
Silver Oxide as a Novel Catalyst for Carbon-Carbon Bond-forming Reactions in Aqueous Media
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DOI：
10.1246/cl.2010.652
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发表时间：
2010-05
影响因子：
1.6
通讯作者：
M. Ueno;Arata Tanoue;S. Kobayashi
中科院分区：
文献类型：
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作者：
M. Ueno;Arata Tanoue;S. Kobayashi
在水介质中，氧化银对烯丙基三丁基锡与醛的烯丙化反应具有很好的催化作用。尽管氧化银在介质中的溶解度很低，但反应进行得很顺利，催化剂被回收和重复使用。当以α-甲基取代的烯丙基三丁基锡为亲核剂时，可以高产率地得到相应的α-加合物，并具有良好的抗选择性。提出了锡转变为银的反应机理。
Silver oxide was found to be an excellent catalyst for allylation reactions of allyltributyltins with aldehydes in aqueous media. Despite the very low solubility of silver oxide in the media, the reactions proceeded smoothly, and the catalyst was recovered and reused. When α-methyl-substituted allyltributyltin was used as the nucleophile, the corresponding α-adducts were obtained exclusively in high yields with good anti-selectivity. A reaction mechanism including transmetalation from tin to silver is proposed.