Heterogeneous h-BN@Cyclodextrin@Pd(II) nanomaterial: Fabrication, characterization and application as a highly efficient and recyclable catalyst for C—C coupling reactions

Abstract

An efficient and ligand-free method for the Suzuki and Heck cross-coupling reactions has been successfully developed using h-BN-supported palladium as the catalyst. This green methodology represents a cost-effective and operationally convenient process for the synthesis of biaryls, stilbenes and acrylates. Wide scope of substrates, good to excellent yields, low reaction time, water as solvent, ligand-free, non-toxicity and recyclability of the catalyst are the main merits of these protocols. In addition, the h-BN@γ-CD@Pd(II) nanomaterial has been fully characterized by TG, SEM, IR, XRD, XPS and ICP-AES analysis. And it could be easily recovered and reused for at least nine times without any considerable loss of catalytic activity. Above all, this work demonstrates the possibility of using cyclodextrin-modified h-BN as an efficient support for the hydrophilic heterogeneous catalysts.

Keywords

Hexagonal boron nitride / Cyclodextrin / Heterogeneous catalysis / C—C cross coupling / Water

References

[1] Golberg D., Bando Y., Huang Y., Terao T., Mitome M., Tang C. C., Zhi C. Y. ACS Nano, 2010, 4: 2979.

[2] Sato K., Horibe H., Shirai T., Hotta Y., Nakano H., Nagai H., Mit-suishi K., Watari K. J. Mater. Chem., 2010, 20: 2749.

[3] Ishida H., Rimdusit S. Thermochim. Acta, 1998, 320: 177.

[4] Xu Y. S., Chung D. D. L. Compos. Interfaces, 2000, 7: 243.

[5] Morishita T., Matsushita M., Katagiri Y., Fukumori K. J. Mater. Chem., 2011, 21: 5610.

[6] Yung K. C., Liem H. J. Appl. Polym. Sci., 2007, 106: 3587.

[7] Li T. L., Hsu S. L. C. J. Phys. Chem. B., 2010, 114: 6825.

[8] Wattanakul K., Manuspiya H., Yanumet N. J. Appl. Polym. Sci., 2011, 119: 3234.

[9] Song L., Ci L. J., Lu H., Sorokin P. B., Jin C. H., Ni J., Kvashnin A. G., Kvashnin D. G., Lou J., Yakobson B. I., Ajayan P. M. Nano Lett., 2010, 10: 3209.

[10] Golberg D., Bando Y., Huang Y., Xu Z., Wei X., Bourgeois L., Wang M. S., Zeng H., Lin J., Zhi C. Isr. J. Chem., 2010, 50: 405.

[11] Ooi N., Rajan V., Gottlieb J., Catherine Y., Adams J. B. Mater. Sci. Eng., 2006, 14: 515.

[12] Hernández E., Goze C., Bernier P., Rubio A. Phys. Rev. Lett., 1998, 80: 4502.

[13] Suryavanshi A. P., Yu M. F., Wen J., Tang C., Bando Y. Appl. Phys. Lett., 2004, 84: 2527.

[14] Kim P., Shi L., Majumdar A., McEuen P. Phys. Rev. Lett., 2001, 87: 215502.

[15] Blase X., Rubio A., Louie S. G., Cohen M. L. Europhys. Lett., 1994, 28: 335.

[16] Watanabe K., Taniguchi T., Kanda H. Nat. Mater., 2004, 3: 404.

[17] Lee G. W., Park M., Kim J., Lee J. I., Yoon H. G. Composites, Part A, 2006, 37: 727.

[18] Pezzotti G., Kamada I., Miki S. J. Eur. Ceram. Soc., 2000, 20: 1197.

[19] Kim K. K., Hsu A., Jia X., Kim S. M., Shi Y., Dresselhaus M., Pala-cios T., Kong J. ACS Nano, 2012, 6: 8583.

[20] Leenders S. H. A. M., Gramage-Doria R., de Bruin B., Reek J. N. H. Chem. Soc. Rev., 2015, 44: 433.

[21] Du Z., Shao Z. Chem. Soc. Rev., 2013, 42: 1337.

[22] Du Bois M. R. Chem. Rev., 1989, 89: 1.

[23] Han F. S. Chem. Soc. Rev., 2013, 42: 5270.

[24] Kotha S., Lahiri K., Kashinath D. Tetrahedron., 2002, 58: 9633.

[25] Zhou X. B., Chen M., Zheng Z. Y., Zhu G. Y., Jiang Z. H., Bai L. P. RSC Adv., 2017, 7: 26921.

[26] Heck R. F., Nolley Jr J. P. J. Org. Chem., 1972, 37: 2320.

[27] Cabri W., Candiani I. Acc. Chem. Res., 1995, 28: 2.

[28] Beletskaya I. P., Cheprakov A. V. Chem. Rev., 2000, 100: 3009.

[29] Cartney D. M., Guiry P. J. Chem. Soc. Rev., 2011, 40: 5122.

[30] Leowanawat P., Zhang N., Safi M., Hoffman D., Fryberger M., George A., Percec V. J. Org. Chem., 2012, 77: 2885.

[31] Suzuki A. Angew. Chem. Int. Ed., 2011, 50: 6722.

[32] Beller M. Chem. Soc. Rev., 2011, 40: 4891.

[33] Chinchilla R., Nájera C. Chem. Soc. Rev., 2011, 40: 5084.

[34] Alsaber P. G., Stradiotto M. Angew. Chem. Int. Ed., 2013, 52: 7242.

[35] Alsabeh P. G., Lundgren R. J., McDonald R. J., Seechurn C. C. C., Colacot T. J., Stradiotto M. Chem. Eur. J., 2013, 19: 2131.

[36] Johansson Seechurn C. C. C., Kitching M. O., Colacot T. J., Snieckus V. Angew. Chem. Int. Ed., 2012, 51: 5062.

[37] Li H. B., Johansson Seechurn C. C. C., Colacot T. J. ACS Catal., 2012, 2: 1147.

[38] Schranck J., Tlili A., Neumann H., Alsabeh P. G., Stradiotto M., Beller M. Chem. Eur. J., 2012, 18: 15592.

[39] Negishi E. I. Angew. Chem. Int. Ed., 2011, 50: 6738.

[40] Fortman G. C., Nolan S. P. Chem. Soc. Rev., 2011, 40: 5151.

[41] Molnar A. Chem. Rev., 2011, 111: 2251.

[42] Zhang Y. M., Zhang J., Li X. F., Chu G., Tian M. M., Qun C. S. Chem. J. Chinese Universities, 2016, 37(3): 573.

[43] Zhou W. J., Zhou Y., Zhang X. Z., Zeng B. Chem. J. Chinese Universities, 2016, 37(4): 669.

[44] Yin J., Ding S. M., Zeng L., Xia H., Chen C., Zhang N. Chem. J. Chinese Universities, 2015, 36(4): 720.

[45] Phan N. T. S., Van Der Sluys M., Jones C. W. Adv. Synth. Catal., 2006, 348: 609.

[46] Andersen N. G., Keay B. A. Chem. Rev., 2001, 101: 997.

[47] Martin R., Buchwald S. L. Acc. Chem. Res., 2008, 41: 1461.

[48] Miyaura N., Suzuki A. Chem. Rev., 1995, 95: 2457.

[49] Liu J., Alvarez J., Ong W., Roman E., Kaifer A. E. Langmuir, 2001, 17: 6762.

[50] Mhadgut S. C., Palaniappan K., Thimmaiah M., Hackney S. A., Torok B., Liu J. Chem. Commun., 2005, 25: 3207.

[51] Hapiot F., Tilloy S., Monflier E. Chem. Rev., 2006, 106: 767.

[52] Machut C., Patrigeon J., Tilloy S., Bricout H., Hapiot F., Monflier E. Angew. Chem. Int. Ed., 2007, 46: 3040.

[53] Zhang X. B., Wang Y., Yang S. T. Carbohydr. Polym., 2014, 114: 521.

[54] Del Valle E. M. M. Process Biochem., 2004, 39: 1033.

[55] Senra J. D., Malta L. F. B., Souza A. L. F., Aguiar L. C. S., Antunes O. A. C. Adv. Synth. Catal., 2008, 350: 2551.

[56] Yabe Y., Yamada T., Nagata S., Sawama Y., Monguchi Y., Sajiki H. Adv. Synth. Catal., 2012, 354: 1264.

[57] Yabe Y., Sawama Y., Monguchi Y., Sajiki H. Chem. Eur. J., 2013, 19: 484.

[58] Uosaki K., Elumalai G., Noguchi H., Masuda T., Lyalin A., Nakaya-ma A., Taketsugu T. J. Am. Chem. Soc., 2014, 136: 6542.

[59] Yabe Y., Sawama Y., Yamada T., Nagata S., Monguchi Y., Sajiki H. ChemCatChem., 2013, 5: 2360.

[60] Meyer L., Devillers M., Hermans S. Catal. Today, 2015, 241: 200.

[61] Meyer N., Bekaert K., Pirson D., Devillers M., Hermans S. Catal. Commun., 2012, 29: 170.

[62] Kumar R., Gopalakrishnan K., Ahmad I., Rao C. N. R. Adv. Funct. Mater., 2015, 25: 5910.

[63] Wu H. C., Kessler M. R. ACS Appl. Mater. Interfaces, 2015, 7: 5915.

[64] Sainsbury T., Satti A., May P., O’Neill A., Nicolosi V. G. Y. K., Coleman J. N. Chem. Eur. J., 2012, 18: 10808.

[65] Cui Z. H., Oyer A. J., Glover A. J., Schniepp H. C., Adamson D. H. Small, 2014, 10: 2352.

[66] Oh K. H., Lee D., Choo M. J., Park K. H., Jeon S., Hong S. H., Park J. K., Choi J. W. ACS Appl. Mater. Interfaces, 2014, 6: 7751.

[67] Cui Z. H., Martinezb A. P., Adamson D. H. Nanoscale, 2015, 7: 10193.

[68] Yang N., Xu C., Hou J., Yao Y. M., Zhang Q. X., Grami M. E., He L. Q., Wang N. Y., Qu X. W. RSC Adv., 2016, 6: 18279.

[69] Lei W. W., Mochalin V. N., Liu D., Qin S., Gogotsi Y., Chen Y. Nat. Commun., 2016, 6: 8849.

[70] Prous J., Castaner J. Drugs Fut., 1987, 12: 120.

[71] Zhu J., Zhu H., Kobamoto N., Yasuda M., Tawata S. J. Pestic. Sci., 2000, 25: 263.

[72] Davis D. C., Mohammad H., Kyei-Baffour K., Younis W., Creemer C. N., Seleem M. N., Dai M. J. Eur. J. Med. Chem., 2015, 101: 384.