Diphenylphosphine Functionalized Graphene Oxide Supported Palladium Complex Catalyzed Heck Coupling Reaction†

doi:10.7503/cjcu20170086

Abstract

Abstract:

The graphene oxide was functionalized by diphenylphosphine through covalent bond. The functio-nalized graphene oxide was used to immobilize palladium via the coordination bonds between the diphenylphosphine and palladium. The as-synthesized catalyst(GO-P-Pd) was characterized by Fourier transform infrared spectroscopy(FTIR), X-ray diffraction(XRD) and X-ray photoelectron spectroscopy(XPS) and applied in the Heck coupling reaction. The result shows that GO-P-Pd exhibits excellent catalytic performance with high activity and stability. And the catalyst can also be applied to catalyze a wide scope of substrates.

Key words: Graphene oxide, Heck coupling reaction, Pd(Ed.: V, Z, K)

CLC Number:

O643.3

TrendMD:

HU Jingwei, CHENG Rui, DING Shunmin, XU Mengmeng, XU Lu, XIAO Weiming, ZHOU Penghui, ZHANG Ning. Diphenylphosphine Functionalized Graphene Oxide Supported Palladium Complex Catalyzed Heck Coupling Reaction^†[J]. Chem. J. Chinese Universities, 2017, 38(9): 1627.

Figures/Tables 7

Scheme 1 Synthetic routes of GO-P-Pd

Fig.1 FTIR spectra of the synthesized samples a. GO; b. GO-APTS; c. GO-P; d. GO-P-Pd.

Fig.2 XRD patterns of the synthesized samplesa. GO; b. GO-APTS; c. GO-P; d. GO-P-Pd.

Fig.3 XPS spectra of GO-P and GO-P-PdSurvey curves: a. GO-P; b. GO-P-Pd; (B) the high resolution curves of the P2p area: a. GO-P; b. GO-P-Pd; (C) the high resolution curves of Pd3d area: a. GO-P-Pd.

Fig.4 Heck reaction of styrene with iodobenzene catalyzed by Pd(OAc)2 and GO-P-Pd(A) and the digital image of GO-P-Pd dispersed in DMSO(B)

Fig.5 Reusability(A) and filtering experiment(B) of GO-P-Pd catalyst in the reaction of styrene with iodobenzene

Table 1 Heck reactions of different olefins with iodobenzene catalyzed by GO-P-Pda

Entry	R	t/h	Yield^b(%)	Entry	R	t/h	Yield^b(%)
1	Ph	6	99	6	COOⁿC₄H₉	2	99
2	4-ClPh	10	97	7	COOⁱC₄H₉	2	99
3	4-CH₃Ph	10	99	8	n-C₄H₉	24	93
4	COOCH₃	2	93	9	n-C₆H₁₃	24	91
5	COOC₂H₅	2	99	10	n-C₈H₁₇	24	87

References 24

[1]	Obuya E. A., Harrigan W., Andala D. M., Lippens J., Keane T. C., Jones Jr W. E., J. Mol. Catal. A: Chem., 2011, 340, 89—98
[2]	Mukhopadhyay S., Rothenberg G., Joshi A., Baidossi M., Sasson Y., Adv. Synth. Catal., 2002, 344, 348—354
[3]	Tsutomu M., Kunio M., Atsumu O., Bull. Chem. Soc. Jpn., 1971, 44, 581—581
[4]	Heck R. F., Nolley J. P., J. Org. Chem., 1972, 37, 2320—2322
[5]	Beletskaya I. P., Cheprakov A. V., Chem. Rev., 2000, 100, 3009—3066
[6]	Bradshaw M., Zou J., Byrne L., Iyer K. S., Stewart S. G., Raston C. L., Chem. Commun., 2011, 47, 12292—12294
[7]	Gronnow M. J., Luque R., Macquarrie D. J., Clark J. H., Green Chem., 2005, 7, 552—557
[8]	Djakovitch L., Koehler K., J. Am. Chem. Soc., 2001, 123, 5990—5999
[9]	Demel J., Lamac M., Cejka J., Stepnicka P., ChemSusChem,2009, 2, 442—451
[10]	Corma A., Iborra S., LlabresI., Xamena F. X., Monton R., Calvino J. J., Prestipino C., J. Phys. Chem. C, 2010, 114, 8828—8836
[11]	Clark J. H., Macquarrie D. J., Mubofu E. B., Green Chem., 2000, 2, 53—55
[12]	Bernini R., Cacchi S., Fabrizi G., Forte G., Niembro S., Petrucci F., Pleixats R., Prastaro A., Sebastian R. M., Soler R., Tristany M., Vallribera A., Org. Lett., 2008, 10, 561—564
[13]	Zhu Y. W., Shanthi M., Cai W. W., Li X. S., Ji W. S., Jeffrey R. P., Rodney S. R., Adv. Mater., 2010, 22, 3906—3924
[14]	Zhao X. L., Sun H. J., Peng T. J., Chem. J. Chinese Universities, 2016, 37(4), 728—735
	(赵小龙, 孙红娟, 彭同江.高等学校化学学报,2016, 37(4), 728—735)
[15]	Yin J., Ding S. M., Zeng L., Xia H., Chen C., Zhang N., Chem. J. Chinese Universities, 2015, 36(4), 720—724
	(尹洁, 丁顺民, 曾乐, 夏辉, 陈超, 张宁.高等学校化学学报,2015, 36(4), 720—724)
[16]	Rao F. Y., Deng S. J., Chen C., Zhang N., Catal. Commun., 2014, 46, 1—5
[17]	Huang J., Ding S. M., Xiao W. M., Peng Y. D., Deng S. J., Zhang N., Catal. Lett., 2015, 145, 1000—1007
[18]	Ding S. M., Liu X. H, Xiao W. M., Li M. M., Pan Y. N., Hu J. W., Zhang N., Catal. Commun., 2017, 92, 5—9
[19]	Shaughnessy K.H., Kim P., Hartwig J. F., J. Am. Chem. Soc., 1999, 121, 2123—2132
[20]	Yang F. Z., Zhang M., Xie J., Xie D. S., Fu L., Chem. J. Chinese Universities, 2015, 36(5), 914—918
	(杨凤志, 张曼, 谢谨, 谢东升, 傅磊.高等学校化学学报,2015, 36(5), 914—918)
[21]	Deng S. J., Zheng Q., Rao F. Y., Lin L. Z., Zhang N., Chinese J. Inorg. Chem., 2015, 31(6), 1085—1090
	(邓圣军, 郑强, 饶福原, 林凌志, 张宁.无机化学学报,2015, 31(6), 1085—1090)
[22]	Hu Q., Hampsey J. E., Jiang N., Li C., Lu Y., Chem. Mater., 2005, 17, 1561—1569
[23]	Dongil A. B., Bachiller-Baeza B., Guerrero-Ruiz A., Rodríguez-Ramos I., J. Catal., 2011, 282, 299—309
[24]	Ding G., Wang W., Jiang T., Han B., Green Chem., 2013, 15, 3396—3403