Direct C-N coupling of azoles with ethers via oxidative C-H activation under metal-organic framework catalysis

Khoa D. Nguyen; Son H. Doan; Anh N.V. Ngo; Tung T. Nguyen; Nam T.S. Phan

Journal of Industrial and Engineering Chemistry, Vol.44, 136-145, December, 2016

DOI10.1016/j.jiec.2016.08.025 Export Citation

Direct C-N coupling of azoles with ethers via oxidative C-H activation under metal-organic framework catalysis

Khoa D. Nguyen, Son H. Doan, Anh N.V. Ngo, Tung T. Nguyen, and Nam T.S. Phan^†

Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Viet Nam, Vietnam

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A metal.organic framework Fe3O(BPDC)3 was synthesized, and used as a productive heterogeneous catalyst for the direct C-N coupling of azoles with ethers via oxidative C-H activation to produce azole derivatives. The MOF-based catalyst displayed higher catalytic efficiency than many homogeneous catalysts as well as several MOFs in the transformation. The MOF-based catalyst could be reused many times for the synthesis of azole derivatives by the direct C-N coupling of azoles with ethers without a noteworthy deterioration in catalytic efficiency. To the best of our knowledge, this direct C-N coupling reaction was not previously performed in the presence of heterogeneous catalysts.

Keywords:Azoles;Coupling;C-H activation;Fe3O(BPDC)3;Ethers

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[Referenced By]

[1] Rao DN, Rasheed S, Vishwakarma RA, Das P, Chem. Commun., 50, 12911 (2014)

[2] Wang Y, Zhang Y, Yang B, Zhang A, Yao Q, Org. Biomol. Chem., 13, 4101 (2015)

[3] Huang Q, Qin X, Li B, Lan J, Guo Q, You J, Chem. Commun., 50, 13739 (2014)

[4] Aruri H, Singh U, Sharma S, Gudup S, Bhogal M, Kumar S, Singh D, Gupta VK, Kant R, Vishwakarma RA, Singh PP, J. Org. Chem., 80, 1929 (2015)

[5] Chen X, Cui X, Yang F, Wu Y, Org. Lett., 17, 1445 (2015)

[6] Zhu F, Wang ZX, Org. Lett., 17, 1601 (2015)

[7] Sangshetti JN, Khan FAK, Kulkarni AA, Arote R, Patil RH, RSC Adv., 5, 32376 (2015)

[8] Xia Q, Chen W, Qiu H, J. Org. Chem., 76, 7577 (2011)

[9] Evano G, Blanchard N, Toumi M, Chem. Rev., 108(8), 3054 (2008)

[10] Wurtz S, Glorius F, Acc. Chem. Res., 41, 1523 (2008)

[11] Rudolph A, Lautens M, Angew. Chem.-Int. Edit., 48, 2656 (2009)

[12] Gooßen LJ, Deng G, Levy LM, Science, 313, 662 (2006)

[13] Stuart DR, Fagnou K, Science, 316, 1172 (2007)

[14] Li CJ, Acc. Chem. Res., 42, 335 (2009)

[15] Li ZP, Li CJ, J. Am. Chem. Soc., 127(11), 3672 (2005)

[16] Kumar GS, Maheswari CU, Kumar RA, Kantam ML, Reddy KR, Angew. Chem.-Int. Edit., 50, 11748 (2011)

[17] Ghobrial M, Schnurch M, Mihovilovic MD, J. Org. Chem., 76, 8781 (2011)

[18] Xia Q, Chen W, J. Org. Chem., 77, 9366 (2012)

[19] Saidulu G, Kumar RA, Reddy KR, Tetrahedron Lett., 56, 4200 (2015)

[20] Pan S, Liu J, Li H, Wang Z, Guo X, Li Z, Org. Lett., 12, 1932 (2010)

[21] Dhakshinamoorthy A, Asiri AM, Garcia H, Angew. Chem.-Int. Edit., 55, 5414 (2016)

[22] Mahmood A, Guo W, Tabassum H, Zou R, Adv. Eng. Mater., doi:http://dx.doi.org/10.1002/aenm.201600423 (in press). (2016)

[23] Ling Y, Liu H, Jiao J, Feng Y, He Y, ChemPlusChem, 81, 786 (2016)

[24] Gu ZG, Fu H, Neumann T, Xu ZX, Fu WQ, Wenzel W, Zhang L, Zhang J, Woll C, ACS Nano, 19, 977 (2016)

[25] Xia W, Mahmood A, Zou R, Xu Q, Energy Environ. Sci., 8, 1837 (2016)

[26] Yu JC, Cui YJ, Wu CD, Yang Y, Chen BL, Qian GD, J. Am. Chem. Soc., 137(12), 4026 (2015)

[27] Zhang Q, Su J, Feng DW, Wei ZW, Zou XD, Zhou HC, J. Am. Chem. Soc., 137(32), 10064 (2015)

[28] Luo J, Zhang X, Zhang J, ACS Catal., 5, 2250 (2015)

[29] Chughtai AH, Ahmad N, Younus HA, Laypkov A, Verpoort F, Chem. Soc. Rev., 44, 6804 (2015)

[30] Zhang F, Zheng S, Xiao Q, Zhong Y, Zhu W, Lin Z, El-Shall MS, Green Chem., 18, 2900 (2016)

[31] Alegre-Requena JV, Marques-Lopez E, Herrera RP, Diaz DD, CrystEngComm, 18, 3985 (2016)

[32] Dang GH, Dang TT, Le DT, Truong T, Phan NTS, J. Catal., 319, 258 (2014)

[33] Dau PV, Cohen SM, Inorg. Chem., 54(7), 3134 (2015)

[34] Hirao H, Ng WKH, Moeljadi AMP, Bureekaew S, ACS Catal., 5, 3287 (2015)

[35] Ge D, Qu G, Li X, Geng K, Cao X, Gu H, New J. Chem., 40, 5531 (2016)

[36] Chen Y, Ma S, J. Chem. Soc.-Dalton Trans., 45, 9744 (2016)

[37] Cancino P, Vega A, Santiago-Portillo A, Navalon S, Alvaro M, Aguirre P, Spodine E, Garcia H, Catal. Sci. Technol., 6, 3727 (2016)

[38] Wang J, Yang M, Dong W, Jin Z, Tang J, Fan S, Lu Y, Wang G, Catal. Sci. Technol., 6, 161 (2016)

[39] Meyer K, Ranocchiari M, Bokhoven JAV, Energy Environ. Sci., 8, 1923 (2015)

[40] Horiuchi Y, Toyao T, Miyahara K, Zakary L, Van DD, Kamata Y, Kim TH, Lee SW, Matsuoka M, Chem. Commun., 52, 5190 (2016)

[41] Oveisi AR, Khorramabadi-zad A, Daliran S, RSC Adv., 6, 1136 (2016)

[42] Lieu TN, Nguyen KD, Le DT, Truong T, Phan NTS, Catal. Sci. Technol., 6, 5916 (2016)

[43] Zhang Z, Li X, Liu B, Zhao Q, Chen G, RSC Adv., 6, 4289 (2016)

[44] Dan-Hardi M, Chevreau H, Devic T, Horcajada P, Maurin G, Ferey G, Popov D, Riekel C, Wuttke S, Lavalley JC, Vimont A, Boudewijns T, Vos DED, Serre C, Chem. Mater., 24, 2486 (2012)

[45] Phan NTS, Jones CW, J. Mol. Catal. A-Chem., 253(1-2), 123 (2006)

[46] Kim HK, Yun WS, Kim MB, Kim JY, Bae YS, Lee J, Jeong NC, J. Am. Chem. Soc., 137(31), 10009 (2015)