Mild and efficient flavin-catalyzed H2O2 oxidation of tertiary amines to amine N-oxides
Mild and efficient flavin-catalyzed H2O2 oxidation of tertiary amines to amine N-oxides
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DOI：
10.1021/jo980926d
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发表时间：
1998-09-18
影响因子：
3.6
通讯作者：
Bäckvall, JE
中科院分区：
文献类型：
--
作者：
Bergstad, K;Bäckvall, JE
在黄素催化下，H_2O_2氧化叔胺反应温和而高效。8个脂肪胺在快速和选择性反应中被氧化成相应的N-氧化物。与非催化反应相比，所有底物的反应速率都有相当大的提高。使用这个基于环境友好的氧化剂过氧化氢的温和氧化系统，以良好的产率分离了产物N-氧化物。作为催化剂，N-1，N-5-二烷基黄素被用作生物上重要的黄素氧化还原辅因子的类似物。黄素催化所建议的催化循环解释了这样的观察，即除了过氧化氢氧化剂外，启动该过程还需要分子氧。
A mild and highly effective H2O2 oxidation of tertiary amines has been developed by the use of flavin catalysis. Eight aliphatic amines were oxidized to their corresponding N-oxides in fast and selective reactions. For all substrates a considerable rate enhancement was observed compared to the noncatalyzed reactions. The product N-oxides were isolated in good yields using this mild oxidation system based on the environmentally attractive oxidant H2O2. As the catalyst, an N-1,N-5-dialkylated flavin was used as an analogue of the biologically important flavin redox cofactor. The catalytic cycle proposed for the flavin catalysis accounts for the observation that, in addition to the hydrogen peroxide oxidant, molecular oxygen is required for the initiation of the process.