基于氮氧自由基催化的醇选择性氧化反应的研究
摘要
本论文发展了基于氮氧自由基催化剂的醇的温和、高效、高选择性的催化氧化方法。
研究发现在NaNO_2存在下,TEMPO/FeCl_3能够有效地催化氧气将醇定量地、高选择性地氧化为相应的醛或酮。在此基础上,系统地考察了溶剂、抗衡阴离子、温度、压力、催化剂各组分用量等因素对醇的催化氧化的影响。在优化条件下, TEMPO/FeCl_3/NaNO_2催化体系能够将含有C=C双键、N、S杂原子等官能团的醇定量地、高选择性地氧化为相应的醛或酮,并且能够高收率得到产品。采用EPR和计量化学等方法对反应机理进行了研究,初步确定了TEMPO/FeCl_3/NaNO_2催化体系中各个组分作用,并提出了可能的催化循环机理。
研究发现,Cu和Cr离子可以替代TEMPO/FeCl_3/NaNO_2体系中的Fe离子,催化醇的氧气氧化。并在此基础上,系统地考察了溶剂、抗衡阴离子、温度、压力等因素对醇的催化氧化的影响。将TEMPO固载在PEG4600上,考察了PEG-TEMPO/FeCl_3/NaNO_2对醇的催化氧化效果,以及催化剂的循环使用情况。
研究发现,在催化量的NHS存在下,乙酰碘苯能将芳香醇氧化为相应的醛或酮;在计量的NHS存在下,乙酰碘苯能将芳香醇和脂肪醇氧化为相应的活泼酯。在实验的基础上,提出了NHS催化乙酰碘苯选择性氧化醇的反应机理。
Simple, mild, efficient and high selective methods for nitroxyl radical-catalysed alcohol oxidation were developed in the paper.
Initial experiment showed that TEMPO/FeCl_3 can catalyze the selective, quantitative aerobic oxidation of alcohols in the presence of NaNO_2. The effect of various conditions (such as solvent, counterion, temperature, oxygen pressure and so on) on the reaction was studied. Under optimum condition, TEMPO/FeCl_3/NaNO_2 catalysed the selective and mild aerobic oxidation of a broad range of alcohols, which may bear N and S heteroatoms or carbon–carbon double bond, to the corresponding aldehydes and ketones with high yield. On the base of experiments, the roles of TEMPO, NaNO_2 and Fe were confirmed and a plausible mechanism was proposed.
Instead of Fe, TEMPO/Cu/NaNO_2 and TEMPO/Cr/NaNO_2 can also catalyze the selective aerobic oxidation of alcohols. Similarly, the effect of various conditions (such as solvent, counterion, temperature, oxygen pressure and so on) on the reaction was studied. PEG-supported TEMPO was successfully used as a catalyst for the oxidation of benzylic alcohol in the presence of TEMPO/FeCl_3. Forthermore, we investigated the recycleability of the catalyst.
Alcohols were oxidized to corresponding aldehydes and ketones in the presence of catalytic amount of N–Hydroxysuccinimide with
研究发现在NaNO_2存在下,TEMPO/FeCl_3能够有效地催化氧气将醇定量地、高选择性地氧化为相应的醛或酮。在此基础上,系统地考察了溶剂、抗衡阴离子、温度、压力、催化剂各组分用量等因素对醇的催化氧化的影响。在优化条件下, TEMPO/FeCl_3/NaNO_2催化体系能够将含有C=C双键、N、S杂原子等官能团的醇定量地、高选择性地氧化为相应的醛或酮,并且能够高收率得到产品。采用EPR和计量化学等方法对反应机理进行了研究,初步确定了TEMPO/FeCl_3/NaNO_2催化体系中各个组分作用,并提出了可能的催化循环机理。
研究发现,Cu和Cr离子可以替代TEMPO/FeCl_3/NaNO_2体系中的Fe离子,催化醇的氧气氧化。并在此基础上,系统地考察了溶剂、抗衡阴离子、温度、压力等因素对醇的催化氧化的影响。将TEMPO固载在PEG4600上,考察了PEG-TEMPO/FeCl_3/NaNO_2对醇的催化氧化效果,以及催化剂的循环使用情况。
研究发现,在催化量的NHS存在下,乙酰碘苯能将芳香醇氧化为相应的醛或酮;在计量的NHS存在下,乙酰碘苯能将芳香醇和脂肪醇氧化为相应的活泼酯。在实验的基础上,提出了NHS催化乙酰碘苯选择性氧化醇的反应机理。
Simple, mild, efficient and high selective methods for nitroxyl radical-catalysed alcohol oxidation were developed in the paper.
Initial experiment showed that TEMPO/FeCl_3 can catalyze the selective, quantitative aerobic oxidation of alcohols in the presence of NaNO_2. The effect of various conditions (such as solvent, counterion, temperature, oxygen pressure and so on) on the reaction was studied. Under optimum condition, TEMPO/FeCl_3/NaNO_2 catalysed the selective and mild aerobic oxidation of a broad range of alcohols, which may bear N and S heteroatoms or carbon–carbon double bond, to the corresponding aldehydes and ketones with high yield. On the base of experiments, the roles of TEMPO, NaNO_2 and Fe were confirmed and a plausible mechanism was proposed.
Instead of Fe, TEMPO/Cu/NaNO_2 and TEMPO/Cr/NaNO_2 can also catalyze the selective aerobic oxidation of alcohols. Similarly, the effect of various conditions (such as solvent, counterion, temperature, oxygen pressure and so on) on the reaction was studied. PEG-supported TEMPO was successfully used as a catalyst for the oxidation of benzylic alcohol in the presence of TEMPO/FeCl_3. Forthermore, we investigated the recycleability of the catalyst.
Alcohols were oxidized to corresponding aldehydes and ketones in the presence of catalytic amount of N–Hydroxysuccinimide with
引文
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