铜催化芳硼酸与亚磷酸酯在空气下的有氧碳-磷氧化偶联反应

doi:10.6023/cjoc201403048

有机化学 ›› 2014, Vol. 34 ›› Issue (7): 1340-1346.DOI: 10.6023/cjoc201403048 上一篇下一篇

研究论文

铜催化芳硼酸与亚磷酸酯在空气下的有氧碳-磷氧化偶联反应

徐清^a, 贾小娟^a, 李晓慧^a, 孙清^a, 周永波^b, 尹双凤^b, 韩立彪^b,c

a 温州大学化学与材料工程学院温州 325035;
b 湖南大学化学化工学院长沙 410082;
c 产业技术综合研究所(AIST) 筑波茨城305-8565 日本

收稿日期:2014-03-23 修回日期:2014-05-10 发布日期:2014-05-23
通讯作者: 徐清, 韩立彪 E-mail:qing-xu@wzu.edu.cn;libiaohan@yahoo.com
基金资助:
国家自然科学基金（No.20902070）和浙江省自然科学杰出青年基金（No.LR14B020002）资助项目.

Copper-Catalyzed Aerobic Oxidative C-P Coupling of Arylboronic Acids and Diethyl Phosphite under Air

Xu Qing^a, Jia Xiaojuan^a, Li Xiaohui^a, Sun Qing^a, Zhou Yongbo^b, Yin Shuangfeng^b, Han Libiao^b,c

a College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035;
b College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
c National Institute of Advanced Industrial Science and TechnologyAIST), Tsukuba, Ibaraki 305-8565, Japan

Received:2014-03-23 Revised:2014-05-10 Published:2014-05-23
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20902070) and the Natural Science Foundation of Zhejiang Province for Distinguished Young Scholars (No. LR14B020002).

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摘要/Abstract

在Cu（OAc）₂/TMEDA体系催化下，芳硼酸与亚磷酸二乙酯可在室温下以空气为直接氧化剂通过氧化偶联反应生成芳基膦酸酯化合物. 该反应使用较为廉价低毒的铜盐为催化剂，不怕水、不怕氧，底物适用范围较广，目标产物选择性高、收率良好. 因此，与已知金属催化卤代芳烃的碳-磷偶联反应相比是一种相对温和高效的合成芳基膦酸酯的方法.

关键词: 铜催化, 芳硼酸, 亚磷酸酯, 氧化偶联, 碳-磷键构建, 芳基膦酸酯

By using Cu(OAc)₂/TMEDA as the catalyst and air as the direct oxidant, arylboronic acids and diethyl phosphite can readily undergo an aerobic oxidative C-P coupling reaction under air at room temperature to give the useful arylphosphonates. This reaction uses relatively cheaper and less toxic copper salts as the catalyst, tolerates moisture and aerobic conditions. is suitable for a comparatively broad scope of substrates, and can give the target arylphosphonates in high selectivities and good yields. In comparison with conventional metal-catalyzed C-P coupling reactions of aryl halides, it is a relatively mild and efficient method for the synthesis of arylphosphonates.

Key words: copper catalysis, arylboronic acids, diethyl phosphite, oxidative coupling, C-P bond construction, arylphosphonates

引用此文

徐清, 贾小娟, 李晓慧, 孙清, 周永波, 尹双凤, 韩立彪. 铜催化芳硼酸与亚磷酸酯在空气下的有氧碳-磷氧化偶联反应[J]. 有机化学, 2014, 34(7): 1340-1346.

Xu Qing, Jia Xiaojuan, Li Xiaohui, Sun Qing, Zhou Yongbo, Yin Shuangfeng, Han Libiao. Copper-Catalyzed Aerobic Oxidative C-P Coupling of Arylboronic Acids and Diethyl Phosphite under Air[J]. Chin. J. Org. Chem., 2014, 34(7): 1340-1346.

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铜催化芳硼酸与亚磷酸酯在空气下的有氧碳-磷氧化偶联反应

Copper-Catalyzed Aerobic Oxidative C-P Coupling of Arylboronic Acids and Diethyl Phosphite under Air

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