基于四氮配体的铜配合物/TEMPO催化的苄醇与烯丙基醇的氧化反应

doi:10.1016/S1872-2067(14)60161-3

催化学报 ›› 2014, Vol. 35 ›› Issue (11): 1864-1873.DOI: 10.1016/S1872-2067(14)60161-3

基于四氮配体的铜配合物/TEMPO催化的苄醇与烯丙基醇的氧化反应

张淑芳^a,b, 苗成霞^a, 徐大乾^a, 孙伟^a, 夏春谷^a

a 中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室, 甘肃兰州730000;
b 中国科学院大学, 北京100049

收稿日期:2014-05-01 修回日期:2014-06-03 出版日期:2014-11-06 发布日期:2014-11-06
通讯作者: 苗成霞,孙伟
基金资助:
国家自然科学基金(21103207,21133011).

CuI/N4 ligand/TEMPO derivatives: A mild and highly efficient system for aerobic oxidation of primary alcohols

Shufang Zhang^a,b, Chengxia Miao^a, Daqian Xu^a, Wei Sun^a, Chungu Xia^a

a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, Gansu, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

Received:2014-05-01 Revised:2014-06-03 Online:2014-11-06 Published:2014-11-06
Supported by:
This work was supported by the National Natural Science Foundation of China (21103207, 21133011).

摘要/Abstract

摘要：

发展了非血红素类四氮配体的铜配合物和2,2,6,6-四甲基哌啶-氮-氧自由基(TEMPO)相结合的催化体系, 应用于分子氧参与的伯醇氧化反应. 该体系具有条件温和、高效、高选择性、无需任何助剂和底物(包括苄醇、烯丙基醇和含杂原子伯醇)使用性强等优点. 此外, 利用高分辨质谱和紫外-光谱等对反应活性中间体进行了初步探讨.

关键词: 醇, 需氧氧化, 四氮配体, 铜, 2,2,6,6-四甲基哌啶-氮-氧自由基

Abstract:

A new system consisting of a copper(I) complex generated in situ from a tetradentate nitrogen ligand and CuI in combination with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) derivatives was successfully developed. The system was suitable for efficient and selective aerobic oxidation of primary benzyl and allyl alcohols with a wide range of functional groups to the corresponding aldehydes at room temperature. The best result was obtained with N,N'-dimethyl-N,N'-bis(2- pyridylmethyl)ethane-1,2-diamine as the ligand and 4-OH-TEMPO as a cocatalyst in CH₃CN. In addition, high-resolution mass spectrometry, ultraviolet-visible spectroscopy, and electrochemical experiments were used to provide evidence of intermediates.

Key words: Alcohol, Aerobic oxidation, Tetradentate nitrogen ligand, Copper, 2,2,6,6-tetramethylpiperidine-1-oxyl

张淑芳, 苗成霞, 徐大乾, 孙伟, 夏春谷. 基于四氮配体的铜配合物/TEMPO催化的苄醇与烯丙基醇的氧化反应[J]. 催化学报, 2014, 35(11): 1864-1873.

Shufang Zhang, Chengxia Miao, Daqian Xu, Wei Sun, Chungu Xia. CuI/N4 ligand/TEMPO derivatives: A mild and highly efficient system for aerobic oxidation of primary alcohols[J]. Chinese Journal of Catalysis, 2014, 35(11): 1864-1873.

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基于四氮配体的铜配合物/TEMPO催化的苄醇与烯丙基醇的氧化反应

CuI/N4 ligand/TEMPO derivatives: A mild and highly efficient system for aerobic oxidation of primary alcohols

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