Regioselective ring opening of styrene oxide by carbon nucleophiles catalyzed by metal?organic frameworks under solvent-free conditions

Nagaraj Anbu; Amarajothi Dhakshinamoorthy

Journal of Industrial and Engineering Chemistry, Vol.58, 9-17, February, 2018

DOI10.1016/j.jiec.2017.08.054 Export Citation

Regioselective ring opening of styrene oxide by carbon nucleophiles catalyzed by metal?organic frameworks under solvent-free conditions

Nagaraj Anbu, and Amarajothi Dhakshinamoorthy^†

School of Chemistry, Madurai Kamaraj University, Madurai-21, India

E-mail:

In the present study, the regioselective ring opening of styrene oxide by indole, aniline, imidazole, pyrrole and benzimidazole as carbon nucleophiles in the presence of Fe(BTC) (BTC: 1,3,5-benzenetricarboxylate)and Cu3(BTC)2 as heterogeneous solid acid catalysts under solvent-free conditions under mild reaction conditions is reported. Furthermore, Fe(BTC) and Cu3(BTC)2 exhibited higher activity under solvent-free conditions than in the presence of solvents. Control experiments with the corresponding homogeneous catalysts reveal the positive role played by the Lewis acids in these MOFs. On the other hand, the activity of these catalysts is significantly reduced in the presence of pyridine, thus, suggesting the involvement of Lewis acid sites. Both Fe(BTC) and Cu3(BTC)2 MOFs show high regioselectivity in the ring opening of styrene oxide by indole. Fe(BTC) and Cu3(BTC)2 are used for four cycles without significant decay in its activity. In addition, comparison of the fresh and four times used Cu3(BTC)2 catalysts by powder XRD and FT-IR indicate the stability of these catalysts under the present experimental conditions. A suitable mechanism is also proposed based on the observed catalytic data.

Keywords:Metal organic frameworks;Ring opening of epoxide;Indole;Heterogeneous catalysis;Lewis acids

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Chui SSY, Lo SMF, Charmant JPH, Orpen AG, Williams ID, Science, 283(5405), 1148 (1999)
Dhakshinamoorthy A, Alvaro M, Horcajada P, Gibson E, Vishnuvarthan M, Vimont A, Greneche JM, Serre C, Daturi M, Garcia H, ACS Catal., 2, 2060 (2012)

[Referenced By]

[1] Parker RE, Isaacs NS, Chem. Rev., 59, 737 (1959)

[2] Buchanan JG, Sable HZ, in: B.S. Thyagarajan (Ed.), Selective Organic Transformations, vol. 2, Wiley, 1972, pp. 1.

[3] Rao AS, Paknikar SK, Kirtane JG, Tetrahedron, 39, 2323 (1983)

[4] Smith JG, Synthesis 629 (1984).

[5] Hirose T, Sunazuka T, Zhi-ming T, Handa M, Vchida R, Shiomi K, Harigaya Y, Omura S, Heterocycles, 53, 777 (2000)

[6] Dhakshinamoorthy A, Alvaro M, Concepcion P, Fornes V, Garcia H, Chem. Commun., 48, 5443 (2012)

[7] Bertozzi F, Crotti P, Macchia F, Pineschi M, Feringa BL, Angew. Chem.-Int. Edit., 40, 930 (2001)

[8] Bandini M, Melloni A, Umani-Ronchi A, Angew. Chem.-Int. Edit., 43, 550 (2004)

[9] Eur. J. Org. Chem., Pineschi M, Eur. J. Org. Chem. 4979 (2006).

[10] Jung ME, Slowinski F, Tetrahedron Lett., 42, 6835 (2001)

[11] Russell MGN, Baker RJ, Barden L, Beer MS, Bristow L, Howard HB, Broughton B, Knowles M, McAllister G, Patel S, Castro JL, J. Med. Chem., 44, 3881 (2001)

[12] Zhang HC, Ye H, Moretto AF, Brumfield KK, Maryanoff BE, Org. Lett., 2, 89 (2000)

[13] Pindur U, Adam R, J. Heterocycl. Chem., 25, 1 (1988)

[14] Rainier JD, Smith AB, Tetrahedron Lett., 41, 9419 (2000)

[15] Amat M, Hadida S, Pshenichnyi G, Bosch J, J. Org. Chem., 62, 3158 (1997)

[16] Walsh FT, Toupence RB, Ujjainwalla F, Young JR, Goulet MT, Tetrahedron, 57, 5233 (2001)

[17] Dirlam JP, Clark DA, J. Org. Chem., 51, 4914 (1986)

[18] Kotsuki H, Hayakawa H, Wakao M, Shimanouchi T, Ochi M, Tetrahedron: Asymmetry, 6, 2665 (1995)

[19] Kotsuki H, Hayashida K, Shimanouchi T, Nishizawa H, J. Org. Chem., 61, 984 (1996)

[20] Tanis SP, Ragion JW, J. Org. Chem., 52, 819 (1987)

[21] Kantam ML, Laha S, Yadav J, Sreedhar B, Tetrahedron Lett., 47, 6213 (2006)

[22] Bandgar BP, Patil AV, Tetrahedron Lett., 48, 173 (2007)

[23] Bandini M, Cozzi PG, Melchiorre P, Umani-Ronchi A, J. Org. Chem., 67, 5386 (2002)

[24] Yadav JS, Reddy BVS, Abraham S, Sabitha G, Synlett, 1550 (2002).

[25] Acocella MR, Mauro M, Guerra G, ChemSusChem, 7, 3279 (2014)

[26] Cook TR, Zheng YR, Stang PJ, Chem. Rev., 113(1), 734 (2013)

[27] Ha PTM, Le BTT, To TC, Doan SH, Nguyen TT, Phan NTS, J. Ind. Eng. Chem., 54, 151 (2017)

[28] Nguyen KD, Doan SH, Ngo ANV, Nguyen TT, Phan NTS, J. Ind. Eng. Chem., 44, 136 (2016)

[29] Bao C, Zhou L, Shao Y, Wu Q, Zhu H, Li K, J. Ind. Eng. Chem., 38, 132 (2016)

[30] Dhakshinamoorthy A, Alvaro M, Garcia H, Catal. Sci. Technol., 1, 856 (2011)

[31] Dhakshinamoorthy A, Garcia H, Chem. Soc. Rev., 43, 5750 (2014)

[32] Wang C, Liu X, Demir NK, Chen JP, Li K, Chem. Soc. Rev., 45, 5107 (2016)

[33] Dhakshinamoorthy A, Alvaro M, Garcia H, Chem. Eur. J., 16, 8530 (2010)

[34] Zhou YX, Chen YZ, Hu Y, Huang G, Yu SH, Jiang HL, Chem. Eur. J., 20, 14976 (2014)

[35] Liu Y, Klet RC, Hupp JT, Farha O, Chem. Commun., 52, 7806 (2016)

[36] Tanabe KK, Cohen SM, Inorg. Chem., 49(14), 6766 (2010)

[37] Beyzavi MH, Klet RC, Tussupbayev S, Borycz J, Vermeulen NA, Cramer CJ, Stoddart JF, Hupp JT, Farha OK, J. Am. Chem. Soc., 136(45), 15861 (2014)

[38] Jiang D, Mallat T, Krumeich F, Baiker A, J. Catal., 257(2), 390 (2008)

[39] Rani P, Srivastava R, RSC Adv., 5, 28270 (2015)

[40] Thornburg NE, Liu Y, Li P, Hupp JT, Farha OK, Notestein JM, Catal. Sci. Technol., 6, 6480 (2016)

[41] Xi W, Liu Y, Xia Q, Li Z, Cui Y, Chem. Eur. J., 21, 12581 (2015)

[42] Juliao D, Barbosa ADS, Peixoto AF, Freire C, de Castro B, Balula SS, Cunha-Silva L, CrystEngComm, 19, 4219 (2017)

[43] Ai J, Min X, Gao CY, Tian HR, Dang S, Sun ZM, Dalton Trans., 6756 (2017).

[44] Sahap D, Hazra DK, Maity T, Koner S, Inorg. Chem., 55(12), 5729 (2016)

[45] Hu Z, Peng Y, Tan KM, Zhao D, CrystEngComm, 17, 7124 (2015)

[46] Tanaka K, Otani KI, Murase T, Nishihote S, Urbanczyk-Lipkowska Z, Bull. Chem. Soc. Jpn., 85, 709 (2012)

[47] Thornburg NE, Liu Y, Li P, Hupp JT, Farha OK, Notestein JM, Catal. Sci. Technol., 6, 6480 (2016)

[48] Tabatabaeian K, Zanjanchi MA, Mahmoodi NO, Eftekhari T, Lett. Org. Chem., 14, 207 (2017)

[49] Horcajada P, Surble S, Serre C, Hong CY, Seo YK, Chang JS, Greneche JM, Margiolaki I, Ferey G, Chem. Commun., 2820 (2007).

[50] Chui SSY, Lo SMF, Charmant JPH, Orpen AG, Williams ID, Science, 283(5405), 1148 (1999)

[51] Dhakshinamoorthy A, Alvaro M, Horcajada P, Gibson E, Vishnuvarthan M, Vimont A, Greneche JM, Serre C, Daturi M, Garcia H, ACS Catal., 2, 2060 (2012)