Oxidative C–H amination reactions

Louillat, Marie‐Laure; Patureau, Frédéric W.

doi:10.1039/c3cs60318k

Cited by 752 publications

(219 citation statements)

References 84 publications

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“…Such a reaction is desirable since it would be highly practical from a synthetic viewpoint and also sustainable, provided that O 2 can be utilized as sole terminal oxidant. [7] In the course of our recent research efforts in the field of reactions for the formation of CÀN bonds, a strategic connectivity in organic synthesis, [8][9][10] we have turned our attention to phenols, an important class of compounds in the food, material, and pharmaceutical industries. [11] Our original idea was to apply Ru-catalyzed C À H-activating amination techniques that we had previously developed.…”

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confidence: 99%

O₂‐mediated dehydrogenative amination of phenols

2015

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A method was developed for the direct dehydrogenative construction of CN bonds between unprotected phenols and a series of cyclic anilines without resorting to any kind of metal activation of either substrate and without the use of halides. The resulting process relies on the exclusively organic activation of molecular oxygen and the subsequent oxidation of the aniline substrate. This allows the coupling of ubiquitous phenols, thus furnishing aminophenols through an atom-economical and most sustainable dehydrogenative amination method. This new reactivity, which relies on the intrinsic organic reactivity of cumene in what can be seen as a modified Hock activation process of oxygen, is expected to have a large impact on the formation of CN bonds in organic synthesis.

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O₂‐mediated dehydrogenative amination of phenols

2015

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“…[1] Metal nitrenei nsertion [2] is the most exploited strategy for this purpose. Alternative methods including metal-free organonitrenoid, [3] CÀHa ctivation/amination [4] and even enzymecatalysis [5] are also emerging. However, these methods are confronted with selectivity issues [6] in intermolecular benzylic CÀHa minations due to the existence of more reactive C(sp2)ÀHb onds.…”

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“…However, these methods are confronted with selectivity issues [6] in intermolecular benzylic CÀHa minations due to the existence of more reactive C(sp2)ÀHb onds. Oxidative CÀHa ctivation/amination reaction, [4] which takes advantage of the propensity of the benzylic CÀHb onds in H-atom abstraction( HAA), has met with some encouraging success. [7] Ritter-type reactions [8] proceed through the nitrile captureo f ac arbon cation intermediate, thusc onstituting another type of oxidative CÀHa mination strategy.F or example, Li and coworkers reporteda ni nteresting Rh-catalyzedd iamination of alkenes by acetonitrile to access imidazolines.…”

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Cu/Fe Catalyzed Intermolecular Oxidative Amination of Benzylic C−H Bonds

Liu

Zhang

et al. 2016

Chemistry A European J

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We report a Cu/Fe co-catalyzed Ritter-type C-H activation/amination reaction that allows efficient and selective intermolecular functionalization of benzylic C-H bonds. This new reaction is featured by simple reaction conditions, readily available reagents and general substrate scope, allowing facile synthesis of biologically interesting nitrogen containing heterocycles. The Cu and Fe salts were found to play distinct roles in this cooperative catalysis.

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“…分子内交叉脱氢偶联作为 C-N 键形成的一种方式越来越受到人们的关注, 这是因为在反应过程中不论是 C-H 键, 还是 N-H 键都不需要预先活化 [1] . 对于金属催化剂, 例如 Pd [2] , Cu [3] 和 Ru [4] 都有报道指出其对分子内交叉脱氢偶联形成新的 C-N 键具有很好的催化活性.…”

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