Pd/SiC催化碘代芳烃和芳基硼酸羰化Suzuki偶联反应性能

引用本文: 崔艳丽, 郭晓宁, 王英勇, 郭向云. Pd/SiC催化碘代芳烃和芳基硼酸羰化Suzuki偶联反应性能[J]. 催化学报, 2015, 36(3): 322-327. doi: 10.1016/S1872-2067(14)60258-8 shu

Citation: Yanli Cui, Xiaoning Guo, Yingyong Wang, Xiangyun Guo. Carbonylative Suzuki coupling reactions of aryl iodides with arylboronic acids over Pd/SiC[J]. Chinese Journal of Catalysis, 2015, 36(3): 322-327. doi: 10.1016/S1872-2067(14)60258-8 shu

Pd/SiC催化碘代芳烃和芳基硼酸羰化Suzuki偶联反应性能

崔艳丽 ^a,b, ,
郭晓宁 ^{a,
,} ,
王英勇 ^a, ,
郭向云 ^a,

通讯作者: 郭晓宁

基金项目:
国家自然科学基金(21203233) (21203233)

山西省自然科学基金(2013021007-1). (2013021007-1)

摘要: 以高比表面积碳化硅为载体, 通过液相还原法制备出Pd/SiC催化剂, 并用于催化碘代芳烃和芳基硼酸羰化Suzuki偶联反应.利用X射线衍射、电感耦合等离子体质谱和高分辨透射电子显微镜等对催化剂进行了表征.结果表明, SiC表面的Pd纳米颗粒分散均匀, 平均粒径约为2.8 nm.在优化溶剂、碱、压力和温度等反应条件后, 发现以3 mmol的K₂CO₃和10 mL苯甲醚分别为碱和溶剂, 1.0 mmol碘苯和1.5 mmol苯硼酸在 3 wt% Pd/SiC催化剂存在的条件下, 在CO压力为1.0 MPa和100 ℃下反应8 h即可实现羰化偶联, 碘苯转化率为90%, 二苯甲酮选择性为99%.并且, Pd/SiC对含有不同官能团的碘代芳烃和芳基硼酸羰化Suzuki偶联反应具有较好的普适性.同时, Pd/SiC也具有较好的稳定性, 经5次循环反应后, 碘苯转化率从90%降至76%; 催化剂活性降低的主要原因是活性组分Pd在有机反应体系中的流失.

关键词:

English

Carbonylative Suzuki coupling reactions of aryl iodides with arylboronic acids over Pd/SiC

1.
a State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, Shanxi, China;

Corresponding author: 郭晓宁

Received Date: 14 September 2014
Available Online: 20 March 2015
Fund Project:
国家自然科学基金(21203233)

山西省自然科学基金(2013021007-1).

Abstract: High surface area SiC has been used to prepare a Pd/SiC catalyst using the liquid reduction method, and the resulting catalyst was used for the carbonylative Suzuki coupling reaction of aryl iodides with arylboronic acids. The catalyst was also characterized by X-ray diffraction, inductively coupled plasma-mass spectroscopy and high-resolution transmission electron microscopy. The results of these analyses showed that homogeneous Pd nanoparticles with a mean diameter of 2.8 nm were uniformly dispersed on the SiC surface. Optimization of the reaction conditions for the carbonylative Suzuki coupling reaction, including the solvent, base, pressure, temperature and reaction time, revealed that the model reaction of iodobenzene (1.0 mmol) with phenylboronic acid (1.5 mmol) could reach 90% conversion with a selectivity of 99% towards the diphenyl ketone using 3 wt% Pd/SiC under 1.0 MPa of CO pressure at 100 ℃ for 8 h with K₂CO₃ (3.0 mmol) as the base and anisole as the solvent. The Pd/SiC catalyst exhibited broad substrate scope towards the carbonylative Suzuki coupling reaction of aryl iodides with arylboronic acids bearing a variety of different substituents. Furthermore, the Pd/SiC catalyst exhibited good recyclability properties and could be recovered and reused up to five times with the conversion of iodobenzene decreasing only slightly from 90% to 76%. The decrease in the catalytic activity after five rounds was attributed to the loss of active Pd during the organic reaction.

Key words:

1. [1] Wang X J, Zhang L, Sun X F, Xu Y B, Krishnamurthy D, Senanayake C H. Org Lett, 2005, 7: 5593[1] Wang X J, Zhang L, Sun X F, Xu Y B, Krishnamurthy D, Senanayake C H. Org Lett, 2005, 7: 5593
2. [2] Hatano B, Kadokaw J, Tagaya H. Tetrahedron Lett, 2002, 43: 5859[2] Hatano B, Kadokaw J, Tagaya H. Tetrahedron Lett, 2002, 43: 5859
3. [3] Gmouh S, Yang H L, Vaultier M. Org Lett, 2003, 5: 2219[3] Gmouh S, Yang H L, Vaultier M. Org Lett, 2003, 5: 2219
4. [4] Yamamoto T, Kohara T, Yamamoto A. Chem Lett, 1976, 11: 1217[4] Yamamoto T, Kohara T, Yamamoto A. Chem Lett, 1976, 11: 1217
5. [5] Hatanaka Y, Fukushima S, Hiyama T. Tetrahedron, 1992, 48: 2113[5] Hatanaka Y, Fukushima S, Hiyama T. Tetrahedron, 1992, 48: 2113
6. [6] Brunet J J, Chauvin R. Chem Soc Rev, 1995, 24: 89[6] Brunet J J, Chauvin R. Chem Soc Rev, 1995, 24: 89
7. [7] Fillion E, Fishlock D, Wilsily A, Goll J M. J Org Chem, 2005, 70: 1316[7] Fillion E, Fishlock D, Wilsily A, Goll J M. J Org Chem, 2005, 70: 1316
8. [8] Jang D O, Moon K S, Cho D H, Kim J G. Tetrahedron Lett, 2006, 47: 6063[8] Jang D O, Moon K S, Cho D H, Kim J G. Tetrahedron Lett, 2006, 47: 6063
9. [9] Ishiyama T, Kizaki H, Miyaura N, Suzuki A. Tetrahedron Lett, 1993, 34: 7595[9] Ishiyama T, Kizaki H, Miyaura N, Suzuki A. Tetrahedron Lett, 1993, 34: 7595
10. [10] Ishiyama T, Kizaki H, Hayashi T, Suzuki A, Miyaura N. J Org Chem, 1998, 63: 4726[10] Ishiyama T, Kizaki H, Hayashi T, Suzuki A, Miyaura N. J Org Chem, 1998, 63: 4726
11. [11] Khedkar M V, Sasaki T, Bhanage B M. RSC Adv, 2013, 3: 7791[11] Khedkar M V, Sasaki T, Bhanage B M. RSC Adv, 2013, 3: 7791
12. [12] Niu J R, Liu M M, Wang P, Long Y, Xie M, Li R, Ma J T. New J Chem, 2014, 38: 1471[12] Niu J R, Liu M M, Wang P, Long Y, Xie M, Li R, Ma J T. New J Chem, 2014, 38: 1471
13. [13] Zhan Y Y, Cai G H, Zheng Y, Shen X N, Zheng Y, Wei K M. Acta Phys- Chim Sin (詹瑛瑛, 蔡国辉, 郑勇, 沈小女, 郑瑛, 魏可镁. 物理化学学报), 2008, 24: 171[13] Zhan Y Y, Cai G H, Zheng Y, Shen X N, Zheng Y, Wei K M. Acta Phys- Chim Sin (詹瑛瑛, 蔡国辉, 郑勇, 沈小女, 郑瑛, 魏可镁. 物理化学学报), 2008, 24: 171
14. [14] Li X Y, Wang F G, Pan X L, Bao X H. Chin J Catal (李星运, 王发根, 潘秀莲, 包信和. 催化学报), 2013, 34: 257[14] Li X Y, Wang F G, Pan X L, Bao X H. Chin J Catal (李星运, 王发根, 潘秀莲, 包信和. 催化学报), 2013, 34: 257
15. [15] Liu H T, Li S Q, Zhang S B, Wang J M, Zhou G J, Chen L, Wang X L. Catal Commun, 2008, 9: 51[15] Liu H T, Li S Q, Zhang S B, Wang J M, Zhou G J, Chen L, Wang X L. Catal Commun, 2008, 9: 51
16. [16] Wang Y W, Guo X N, Dong L L, Jin G Q, Wang Y Y, Guo X Y. Int J Hydrogen Energy, 2013, 38: 12733[16] Wang Y W, Guo X N, Dong L L, Jin G Q, Wang Y Y, Guo X Y. Int J Hydrogen Energy, 2013, 38: 12733
17. [17] Zhang G Q, Peng J X, Sun T J, Wang S D. Chin J Catal (张国权, 彭家喜, 孙天军, 王树东. 催化学报), 2013, 34: 1745[17] Zhang G Q, Peng J X, Sun T J, Wang S D. Chin J Catal (张国权, 彭家喜, 孙天军, 王树东. 催化学报), 2013, 34: 1745
18. [18] Li H L, Lei Y G, Huang Y, Fang Y P, Xu Y H, Zhu L, Li X. J Nat Gas Chem, 2011, 20: 145[18] Li H L, Lei Y G, Huang Y, Fang Y P, Xu Y H, Zhu L, Li X. J Nat Gas Chem, 2011, 20: 145
19. [19] Jiao Z F, Guo X N, Zhai Z Y, Jin G Q, Wang X M, Guo X Y. Catal Sci Technol, 2014, 4: 2494[19] Jiao Z F, Guo X N, Zhai Z Y, Jin G Q, Wang X M, Guo X Y. Catal Sci Technol, 2014, 4: 2494

扫一扫看文章

计量

PDF下载量: 199
文章访问数: 783
HTML全文浏览量: 66

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Pd/SiC催化碘代芳烃和芳基硼酸羰化Suzuki偶联反应性能

通讯作者: 郭晓宁

English

Carbonylative Suzuki coupling reactions of aryl iodides with arylboronic acids over Pd/SiC

Corresponding author: 郭晓宁

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

Pd/SiC催化碘代芳烃和芳基硼酸羰化Suzuki偶联反应性能

通讯作者: 郭晓宁

English

Carbonylative Suzuki coupling reactions of aryl iodides with arylboronic acids over Pd/SiC

Corresponding author: 郭晓宁

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs