Preparation and Suzuki Reaction Performance of Pectin-supported Palladium Catalyst†

doi:10.7503/cjcu20150799

Abstract

Abstract:

To discover new heterogeneous palladium catalyst in organic synthesis, pectin, which was extracted form citrus peel, was used as supporter for the preparation of pectin-supported palladium catalyst. The pectin-supported palladium catalyst was applied to Suzuki cross-coupling reaction between sodium tetraphenylborate and aryl bromides. The results revealed that all four aryl groups of sodium tetraryylborate could be efficiently utilized in the Suzuki cross-coupling reactions in an atom-efficient way in the presence of Et₃N as base in PEG 400/H₂O at 110 ℃ in open air, providing excellent yields of the corresponding functionalized biaryls within 1 h. The present protocol has the advantages highly efficient, high yield, mild condition, short reaction time, as well as the catalyst can be recycled and reused.

Key words: Pectin supported-Pd, Suzuki reaction, Sodium tetraphenylborate, Aryl bromide

CLC Number:

O621.25

TrendMD:

ZHOU Wenjun, ZHOU Yu, ZHANG Xiazhong, ZENG Bin. Preparation and Suzuki Reaction Performance of Pectin-supported Palladium Catalyst^†[J]. Chem. J. Chinese Universities, 2016, 37(4): 669.

Figures/Tables 7

References 27

[1]	Miyaura N., Suzuki A., Chem. Rev., 1995, 95(7), 2457—2483
[2]	Littke A. F., Fu G. C., Angew. Chem. Int. Ed., 2002, 41(22), 4176—4211
[3]	Alberico D., Scott M. E., Lautens M., Chem. Rev., 2007, 107(1), 174—238
[4]	Thompson L. A., Ellman J. A., Chem. Rev., 1996, 96(1), 535—600
[5]	Stephen P. S., Tetrahedron, 1998, 54(2), 263—303
[6]	Irina P. B., Pure Appl. Chem., 1997, 69(3), 471—476
[7]	Du W. H., An Z. W., Xu M. L., Mol. Catal., 1997, 11(1), 72—80
	(杜卫红, 安忠维, 徐茂梁. 分子催化, 1997, 11(1), 72—80)
[8]	Miyaura N., Suzuki A., Chem. Rev., 1995, 95(7), 2457—2483
[9]	Phan N. T. S., Vander S. M., Jones C. W., Adv. Synth. Catal., 2006, 348(6), 609—679
[10]	Farina V., Adv. Synth. Catal., 2004, 346(13—15), 1553—1582
[11]	Stanforth S. P., Tetrahedron, 1998, 54(3/4), 263—303
[12]	Nobre S. M., Wolke S. I., da Rosa R. G., Monteiro A. L., Tetrahedron Lett., 2004, 45(36), 6527—6530
[13]	Stevens P.D., Li G., Fan J. D., Yen M., Gao Y.,Chem. Commun., 2005, (35), 4435—4437
[14]	Corma A., García H., Leyva A., J. Catal., 2006, 240(2), 87—99
[15]	Cole-Hamiton D. J., Science, 2003, 299(5613), 1702—1706
[16]	Wei Y. X., Tu W. X., Chem. J. Chinese Universities, 2014, 35(11), 2397—2402
	(魏英祥, 涂伟霞. 高等学校化学学报, 2014, 35(11), 2397—2402)
[17]	Shen L. Q., Huang S. Y., Lei F. H., Huang Z. Y., Chem. J. Chinese Universities, 2013, 34(6), 1428—1433
	(申利群, 黄素玉, 雷福厚, 黄在银. 高等学校化学学报, 2013, 34(6), 1428—1433)
[18]	Yin L., Liebscher J., Chem. Rev., 2007, 107(1), 133—173
[19]	Lamblin M., Hardy-Nassar L., Hierso J. C., Fouquet E., Felpin F. X., Adv. Synth. Catal., 2010, 352(1), 33—79
[20]	Xie M. Y., Li J., Nie S. P., J. Chin. Inst. Food. Sci. Technol., 2013, 13(8), 1—14
	(谢明勇, 李精, 聂少平. 中国食品学报, 2013, 13(8), 1—14)
[21]	Khazaei A., Khazaei M., Rahmati S., J. Mol. Catal. A: Chem., 2015, 398, 241—247
[22]	Khazaei A., Khazaei M., Rahmati S., Catal. Commun., 2013, 37, 9—13
[23]	Khazaei A., Rahmati S., Hekmatian Z., J. Mol. Catal. A: Chem., 2013, 372, 160—166
[24]	Xie F., Wang B., Liu Y. W., Zhou W. J., Huang H., Extraction of Pectin from Lemon Peel by Compound Enzyme Method, CN 201310182117.1, 2013-08-07
	(谢峰, 王碧, 刘义武, 周文俊, 黄辉. 一种利用酶法从柠檬皮渣中提取果胶的方法, CN 201310182117.1, 2013-08-07)
[25]	Zhou Y., He Y., Zhou W. J., Chin. J. Appl. Chem., 2015, 32(12),1042—1049
	(周宇, 何媛, 周文俊. 应用化学, 2015, 32(12), 1042—1049)
[26]	Zhou W. J., Wang K. H., Wang J. X., Huang D. F., Eur. J. Org. Chem., 2010, 2010(3), 416—419
[27]	Son S., Jang Y. G., Park J., J. Am. Chem. Soc., 2004, 126(16), 5026—5027

No.	Cycle	t/min	Yield^b(%)
1	1st	20	88
2	2nd	20	70
3	3rd	40	65
4	4th	60	55

No.	Cycle	t/min	Yield^b(%)
1	1st	20	88
2	2nd	20	70
3	3rd	40	65
4	4th	60	55