Pd/1,3-双(二苯基膦)丙烷催化苯并噁唑C-2位直接芳基化反应的研究

doi:10.6023/cjoc201807050

有机化学 ›› 2019, Vol. 39 ›› Issue (2): 482-490.DOI: 10.6023/cjoc201807050 上一篇下一篇

所属专题：碳氢活化合辑2018-2019

研究论文

Pd/1,3-双(二苯基膦)丙烷催化苯并噁唑C-2位直接芳基化反应的研究

汪洋点点, 余晓军, 付海燕, 郑学丽, 陈华, 李瑞祥

四川大学化学学院教育部绿色化学和技术重点实验室成都 610064

收稿日期:2018-07-27 修回日期:2018-09-05 发布日期:2018-09-10
通讯作者: 李瑞祥 E-mail:liruixiang@scu.edu.cn
基金资助:
国家自然科学基金（Nos.21572137，21871187）、四川省科技厅基金（No.2018GZ0312）资助项目.

Pd/1,3-Bis(diphenylphosphino)propane Catalyzed Arylation of Benzoxazoles at C-2 Position with Aryl Bromides

Wang Yangdiandian, Yu Xiaojun, Fu Haiyan, Zheng Xueli, Chen Hua, Li Ruixiang

Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064

Received:2018-07-27 Revised:2018-09-05 Published:2018-09-10
Contact: 10.6023/cjoc201807050 E-mail:liruixiang@scu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572137, 21871187), the Key Program of Sichuan Science and Technology Project (No. 2018GZ0312).

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1. Pd/1,3-双(二苯基膦)丙烷催化苯并噁唑C-2位直接芳基化反应的研究.PDF(3413KB)

摘要/Abstract

利用简单商业可得的PdCl₂和1，3-双（二苯基膦）丙烷（dppp）作催化剂，高效催化了苯并噁唑和溴苯C-2取代的芳基化反应.该催化体系表现出了很好的官能团容忍性，当催化剂用量为0.1 mol%时，反应6 h收率可达90%以上，更重要的是，当催化剂用量低至0.01 mol%时，通过延长反应时间，转化率仍然能达到90%以上.通过汞中毒实验，透射电镜和X射线光电子能谱证实了该反应是钯纳米粒子催化的过程.此外，通过控制实验证实了底物苯并噁唑在反应过程中经历了开环和关环的途径.最后，通过热过滤和高分辨质谱实验从一定程度上证实了该反应可能经历了Pd（0）-Pd（Ⅱ）的反应历程.

关键词: 芳化反应, 苯并噁唑, 1,3-双(二苯基膦)丙烷, 钯

A catalyst system combined of PdCl₂ with 1,3-bis(diphenylphosphion)propane (dppp), which was simple and from commercially available materials, was reported for the highly efficient arylation of benzoxazoles at C-2 position with aryl bromides. This catalytic system could tolerate a great number of functional groups in benzoxazole and bromobenzene. With a low PdCl₂ loading of 0.01 mol%, aryl bromides could be completely converted into the desired products for 24 h. If the loading of catalyst was up to 0.10 mol%, most of substrates could give more than 90% yields in 6 h. The exploration of the reaction mechanism discovered that Pd nanoparticles were formed during this reaction. The morphology and composition analysis of the Pd nanoparticles with transmission electron microscopy (TEM) and X-ray photoelectron spectroscopy (XPS) indicated that dppp played a key role to block the aggregation of palladium particles. In addition, the ring-opening pathway of benzoxazoles in the reaction process was proved by control experiments. Hot filtration experimental and high resolution mass spectrum (HRMS) analysis of filtrate suggested that the real active species were Pd(0)-Pd(Ⅱ)/dppp complexes.

Key words: arylation, benzoxazole, 1,3-bis(diphenylphosphion)propane, palladium

引用此文

汪洋点点, 余晓军, 付海燕, 郑学丽, 陈华, 李瑞祥. Pd/1,3-双(二苯基膦)丙烷催化苯并噁唑C-2位直接芳基化反应的研究[J]. 有机化学, 2019, 39(2): 482-490.

Wang Yangdiandian, Yu Xiaojun, Fu Haiyan, Zheng Xueli, Chen Hua, Li Ruixiang. Pd/1,3-Bis(diphenylphosphino)propane Catalyzed Arylation of Benzoxazoles at C-2 Position with Aryl Bromides[J]. Chin. J. Org. Chem., 2019, 39(2): 482-490.

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Pd/1,3-双(二苯基膦)丙烷催化苯并噁唑C-2位直接芳基化反应的研究

Pd/1,3-Bis(diphenylphosphino)propane Catalyzed Arylation of Benzoxazoles at C-2 Position with Aryl Bromides

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