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首页> 外文期刊>Catalysis science & technology >Direct hydroxylation of benzene and aromatics with H2O2 catalyzed by a self-assembled iron complex: evidence for a metal-based mechanism
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Direct hydroxylation of benzene and aromatics with H2O2 catalyzed by a self-assembled iron complex: evidence for a metal-based mechanism

机译：苯和芳烃的直接羟基化过氧化氢催化的自组装铁复杂:依据金属机制

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摘要

An iminopyridine Fe(II) complex, easily prepared in situ by self-assembly of cheap and commercially available starting materials (2-picolylaldehyde, 2-picolylamine, and Fe(OTf)(2) in a 2 : 2 : 1 ratio), is shown to be an effective catalyst for the direct hydroxylation of aromatic rings with H2O2 under mild conditions. This catalyst shows a marked preference for aromatic ring hydroxylation over lateral chain oxidation, both in intramolecular and intermolecular competitions, as long as the arene is not too electron poor. The selectivity pattern of the reaction closely matches that of electrophilic aromatic substitutions, with phenol yields and positions dictated by the nature of the ring substituent (electron-donating or electron-withdrawing, ortho-para or meta-orienting). The oxidation mechanism has been investigated in detail, and the sum of the accumulated pieces of evidence, ranging from KIE to the use of radical scavengers, from substituent effects on intermolecular and intramolecular selectivity to rearrangement experiments, points to the predominance of a metal-based SEAr pathway, without a significant involvement of free diffusing radical pathways.
机译：iminopyridine铁(II)复杂,容易准备廉价和原位自组装的商用起始原料(2-picolylaldehyde、2-picolylamine and铁(传递)2(2):2:1比例),显示一个有效的直接的催化剂羟基化的芳香环与过氧化氢温和的条件。偏爱芳环羟基化侧链氧化,在分子内和分子间的比赛,只要芳烃是电子不太穷。反应的模式匹配的亲电芳香取代苯酚收益率和职位由的本质环取代基(电子基或吸电子、邻对位或meta-orienting)。详细调查和之和积累的证据,从KIE使用激进的食腐动物,取代基对分子间和影响分子内选择性,重排实验中,点的优势金属烤焦的途径,没有意义参与自由扩散的根本途径。

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