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首页> 外文期刊>Chemistry: A European journal >Factors Influencing the Regioselectivity of the Oxidation of Asymmetric Secondary Amines with Singlet Oxygen
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Factors Influencing the Regioselectivity of the Oxidation of Asymmetric Secondary Amines with Singlet Oxygen

机译：单线态氧氧化不对称仲胺的区域选择性的影响因素

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Aerobic amine oxidation is an attractive and elegant process for the functionalization of amines. However, there are still several mechanistic uncertainties, particularly the factors governing the regioselectivity of the oxidation of asymmetric secondary amines and the oxidation rates of mixed primary amines. Herein, it is reported that singlet-oxygen-mediated oxidation of 1 degrees and 2 degrees amines is sensitive to the strength of the -CH bond and steric factors. Estimation of the relative bond dissociation energy by natural bond order analysis or by means of one-bond CH coupling constants allowed the regioselectivity of secondary amine oxidations to be explained and predicted. In addition, the findings were utilized to synthesize highly regioselective substrates and perform selective amine cross-couplings to produce imines.
机译：有氧胺氧化是胺官能化的一种有吸引力且优雅的方法。然而，仍然存在一些机械不确定性，特别是控制不对称仲胺氧化的区域选择性和混合伯胺氧化速率的因素。此处，据报道，单线态氧介导的1度和2度胺的氧化对-CH键的强度和空间因素敏感。通过自然键序分析或单键CH偶联常数估算相对键解离能，可以解释和预测仲胺氧化的区域选择性。另外，该发现被用于合成高度区域选择性的底物并进行选择性胺交叉偶联以产生亚胺。

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