Functionalized Graphene Oxide Supported Pd Nanoparticles Catalyzed Heck Coupling Reaction†

doi:10.7503/cjcu20140997

Abstract

Abstract:

Pd nanoparticles were immobilized on a graphene oxide(GO) functionalized by 3-(2-aminoethyl)-aminopropyl trimethoxysilane support. The catalyst was characterized by Fourier transform infrared(FTIR), X-ray diffraction, thermal analysis, elementary analysis, and transmission electron microscopy. The catalyst exhibited a superior catalytic performance in Heck coupling reaction, and was applicable to a wide range of substrates. Recycling experiments showed that the catalyst could be easily recovered by simple centrifugation and reused for up to three cycles without losing its activity.

Key words: Graphene oxide, Pd nanoparticles, 3-(2-Aminoethyl)-aminopropyl trimethoxysilane, Heck coupling reaction

CLC Number:

O643.3

TrendMD:

YIN Jie, DING Shunmin, ZENG Le, XIA Hui, CHEN Chao, ZHANG Ning. Functionalized Graphene Oxide Supported Pd Nanoparticles Catalyzed Heck Coupling Reaction^†[J]. Chem. J. Chinese Universities, 2015, 36(4): 720.

Figures/Tables 9

Scheme 1 Synthesis of Pd@GO-NN

Fig.1 FTIR spectra of GO(a), GO-NN(b)and Pd@GO-NN(c)

Table 1 Elemental analysis of GO, GO-NN and Pd@GO-NN

Sample	Elemental content(%)			N content/(mmol·g^-1)
Sample	C		H	N
GO	52.62	2.87
GO-NN	46.65	4.90	7.31	5.2
Pd@GO-NN	46.25	4.60	7.02	5.0

Fig.2 XRD patterns of GO, GO-NN and Pd@GO-NN (A) a. GO; b. GO-NN; (B) a. GO-NN; b. Pd@GO-NN.

Fig.3 HRTEM image(A) and particle distribution(B) of Pd@GO-NN

Fig.4 TGA curves of GO(a), GO-NN(b)and Pd@GO-NN(c)

Fig.5 Effect of temperature(A) and time(B) in the Heck coupling reaction

Fig.6 Heck coupling reaction catalyzed by Pd@GO-NN(a), Pd@SiO2-NN(b) and Pd@AC-NN(c) Reaction condition: 0.5 mmol iodobenzene, 0.6 mmol styrene, Pd catalyst(0.319% Pd, molar fraction), 0.66 mmol EG, 3.5 mmol MeCOOK, 4 mL DMSO, 120 ℃.

Table 2 Heck reaction with Pd@GO-NN catalysta

Entry	R	Time/h	Yield^b(%)	Entry	R	Time/h	Yield^b(%)
1	Ph	4	99	6	COOⁿC₄H₉	2	99
2	4-ClPh	8	99	7	COOⁱC₄H₉	2	99
3	4-CH₃Ph	10	99	8	n-C₄H₉	10	81
4	COOCH₃	2	99	9	n-C₆H₁₃	10	83
5	COOC₂H₅	2	99	10	n-C₈H₁₇	10	91

References 19

[1]	Heck. R. F., Org. React., 1982, 27, 345—390
[2]	Abramovitch R. A., Barton D. H. R., Finet J. P., Tetrahedron,1988, 44, 3039—3071
[3]	Adam F. L., Gregory C. F., Angew. Chem. Int. Ed., 2002, 41, 4176—4211
[4]	Wang Y. C., Li X. Y., Li Y. J., Pan Y. M., Cheng K. G., Wang H. S., Chem. Res. Chinese Universities,2014, 30(4), 614—618
[5]	Robin B. B., Chem. Commun., 2003, 15, 1787—1796
[6]	Tuyet J., Tetrahedron Lett., 2000, 41, 8445—8449
[7]	Zhu J., Zhou J. H., Zhao T. J., Zhou X. G., Chen D., Yuan W. K., Appl. Catal. A,2009, 352, 243—250
[8]	Cai M. Z., Song C. S., Chem. J. Chinese Universities,1998, 19(10), 1693—1696
	(蔡明中, 宋才生. 高等学校化学学报, 1998, 19(10), 1693—1696)
[9]	Wang P. Y., Wang Z. Y., Li J. G., Bai Y. X., Micropor. Mesopor. Mater., 2008, 116, 400—405
[10]	Toma N. G., Silvia F. C., Oliver K., Chem. Eur. J., 2009, 15, 1001—1010
[11]	Christine Schmöger., Tony Szuppa., Antje Tied., Franziska Schneider., Achim Stolle., Bernd Ondruschka., Chem. Sus. Chem., 2008, 1, 339—347
[12]	Zhu Y. W., Shanthi M., Cai W. W., Li X. S., Ji Won Suk., Jeffrey R. P., Rodney S. R., Adv. Mater., 2010, 22, 3906—3924
[13]	Hermann M., Andreas R., Bjorn G., Christian K., Armin S., Chem. Phys. Lett., 1998, 287, 57—60
[14]	Yu L., Zhang Y. T., Liu J. D., Chem. J. Chinese Universities,2014, 35(5), 1100—1105
	(余亮, 张亚涛, 刘金盾. 高等学校化学学报, 2014, 35(5), 1100—1105)
[15]	Xu Y. X., Bai H., Lu G. W., Li C., Shi G. Q., J. Am. Chem. Soc., 2008, 130, 5856—5857
[16]	Tamás Szabó, Etelka Tombácz, Erzsébet Illés, Imre Dékány, Carbon, 2006, 44, 537—545
[17]	Aline Guimont, Emmanuel Beyou, Gregory Martin, Philippe Sonntag, Philippe Cassagnau, Macromolecule, 2011, 44, 3893—3900
[18]	Chu X. F., Zhu Q. J., Dai W. L., Fan K. N., RSC Adv., 2012, 2, 7135—7139
[19]	Li X. T., Zang P. Y., Ye Q. M., Geng J., Wang X. Z., Wang Y. N., Hu Z., Chinese J. Inorg. Chem., 2011, 27(8), 1550—1554
	(李雪婷, 臧鹏远, 叶秋明, 耿皎, 王喜章, 王秧年, 胡征. 无机化学学报, 2011, 27(8), 1550—1554)