Flavins as organocatalysts for environmentally benign molecular transformations
Flavins as organocatalysts for environmentally benign molecular transformations
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DOI：
10.1002/tcr.20135
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发表时间：
2007-01-01
期刊：
影响因子：
6.6
通讯作者：
Naota, Takeshi
中科院分区：
文献类型：
--
作者：
Imada, Yasushi;Naota, Takeshi
从黄素催化氧化反应的范围、局限性和反应机理等方面介绍了黄素催化氧化反应及相关反应研究的最新进展。4a-羟基过氧基黄素是黄素酶最简单的模型化合物，在H_2O_2或O_2作为温和的氧化剂的帮助下，它们作为催化活性物种氧化有机底物。黄素酶模拟背后的这一原理导致了各种环境友好的氧化转化，仲胺到硝酮，叔胺到N-氧化物，硫化物到亚硫醚，以及酮的Baeyer-Villiger氧化。硫化物的不对称氧化也可以用几种手性黄素催化剂进行。这项研究的幸运成果之一是开发了一种环境友好的(绿色)烯烃“好氧加氢”方法，该方法是在0℃的气氛下，通过黄素催化的联氨氧化原位生成二亚胺来实现的。(C)2007年日本化学期刊论坛和威利期刊公司。
Recent progress in the development of flavin-catalyzed oxidations and related reactions is described with respect to scope, limitation, and reaction mechanism. The 4a-hydroperoxy-flavins, which are the most simplified model compounds of flavoenzymes, act as catalytically active species for the oxidation of organic substrates with the help of H2O2 or O-2 as a mild oxidant. This principle behind the simulation of flavoenzymes led to the discovery of a variety of environmentally benign, oxidative transformations of secondary amines to nitrones, tertiary amines to N-oxides, Sulfides to sulfoxides, and Baeyer-Villiger oxidations of ketones. Asymmetric oxidation of sulfides can also be performed with several chiral flavin catalysts. One of the fortunate outcomes of this study is the development of an environmentally friendly ("green") method for the "aerobic hydrogenation" of olefins, which is achieved by in situ generation of diimide with the aid of the flavin-catalyzed oxidation of hydrazine under an 0, atmosphere. (C) 2007 The Japan Chemical Journal Forum and Wiley Periodicals, Inc.