Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Facile Access to 2-Substituted Benzoxazoles Using Sawdust Supported N-Heterocyclic Carbene-Ni Complex via C-H Activation

Author(s): Dolly Kale, Gajanan Rashinkar, Audumbar Patil, Arjun Kumbhar and Rajashri Salunkhe*

Volume 17, Issue 6, 2020

Page: [479 - 489] Pages: 11

DOI: 10.2174/1570178616666190705153927

Price: $65

Abstract

Sawdust supported N-heterocyclic carbene-nickel complex has been prepared by covalent grafting of 1-methyl imidazole in the matrix of chloropropyl modified sawdust followed by reaction with nickel acetate. The resultant NHC-Ni complex was employed as a heterogeneous catalyst for the synthesis of 2-substituted benzoxazoles from benzoxazole and aryl boronic acids following C-H activation strategy. The recycling experiments showed that the complex could be reused for five consecutive runs without significant loss in the yield of products.

Keywords: C-H activation, N-Heterocyclic carbene, sawdust, benzoxazole, reusability, heterogeneous analogues.

« Previous
Graphical Abstract

[1]
(a)Ofele, K.J. J. Organomet. Chem., 1968, 12, 42-43.
[http://dx.doi.org/10.1016/S0022-328X(00)88691-X]]
(b)Wanzlic, H.W.; Schonherr, H.J. Angew. Chem. Int. Ed. Engl., 1968, 7, 141-142.
[http://dx.doi.org/10.1002/anie.196801412]]
(c)Díez-González, S.; Marion, N.; Nolan, S.P. Chem. Rev., 2009, 109(8), 3612-3676.
[http://dx.doi.org/10.1021/cr900074m] [PMID: 19588961]
(d)Fortman, G.C.; Nolan, S.P. J. Curr. Org. Chem., 2014, 18, 700-718.
[2]
(a)Velazquez, H.D.; Verpoort, F. Chem. Soc. Rev., 2012, 41(21), 7032-7060.
[http://dx.doi.org/10.1039/c2cs35102a] [PMID: 22842861]
(b)Díez-González, S.; Marion, N.; Nolan, S.P. Chem. Rev., 2009, 109(8), 3612-3676.
[http://dx.doi.org/10.1021/cr900074m] [PMID: 19588961]
(c)Cai, X-H.; Xie, B. Mini Rev. Org. Chem., 2018, 15, 248-260.
[http://dx.doi.org/10.2174/1570193X14666171018150710]
[3]
(a)Nelson, D.J.; Nolan, S.P. Chem. Soc. Rev., 2013, 42(16), 6723-6753.
[http://dx.doi.org/10.1039/c3cs60146c] [PMID: 23788114]
(b)Díez-González, S.; Nolan, S.P. Coord. Chem. Rev., 2007, 251, 874-883.
[http://dx.doi.org/10.1016/j.ccr.2006.10.004]]
(c)Würtz, S.; Glorius, F. Acc. Chem. Res., 2008, 41(11), 1523-1533.
[http://dx.doi.org/10.1021/ar8000876] [PMID: 18720995]
(d)Valente, C.; Çalimsiz, S.; Hoi, K.H.; Mallik, D.; Sayah, M.; Organ, M.G. Angew. Chem. Int. Ed., 2012, 51, 3314-3332.
[http://dx.doi.org/10.1002/anie.201106131]
[4]
(a)Cavallo, L.; Correa, A.; Costabile, C.; Jacobsen, H. J. Organomet. Chem., 2005, 690, 5407-5413.
[http://dx.doi.org/10.1016/j.jorganchem.2005.07.012]]
(b)Turkmen, H.; Cetinkaya, B. J. Organomet. Chem., 2006, 691, 3749-3759.
[http://dx.doi.org/10.1016/j.jorganchem.2006.05.020]
[5]
(a)Chemistry, 2015, 21, 12291-12294.
(b)Cazin, C.S.J. J. Catal. Sci. Tech., 2013, 3, 2161-2181.
[6]
(a)Wang, Z.; Yu, Y.; Zhang, Y.X.; Li, S.Z.; Qian, H.; Lin, Z.Y. Green Chem., 2015, 17, 413-420.
[http://dx.doi.org/10.1039/C4GC00574K]
(b)Kim, J-H.; Kim, J-W.; Shokouhimehr, M.; Lee, Y-S. J. Org. Chem., 2005, 70(17), 6714-6720.
[http://dx.doi.org/10.1021/jo050721m] [PMID: 16095291]
(c)Qiu, H.; Sarkar, S.M.; Lee, D-H.; Jin, M-J. Green Chem., 2008, 10, 37-40.
[http://dx.doi.org/10.1039/B712624G]
(d)Zhou, H.; Zhang, Q-Y.; Lu, X-B. RSC Advances, 2016, 6, 44995-45000.
[http://dx.doi.org/10.1039/C6RA07786B]
(e)Shang, N.; Gao, S.; Feng, C.; Zhang, H.; Wang, C.; Wang, Z. RSC Adv., 2013, 21863-21868.
[7]
(a)Crabtree, R.H.; Lei, A. Chem. Rev., 2017, 117(13), 8481-8482.
[http://dx.doi.org/10.1021/acs.chemrev.7b00307] [PMID: 28697603]
(b)Gensch, T.; Hopkinson, M.N.; Glorius, F. J.Chem. Soc. Rev., 2016, 45, 2900-2936.
[http://dx.doi.org/10.1039/C6CS00075D]
(c)Lyons, T.W.; Sanford, M.S. Chem. Rev., 2010, 110(2), 1147-1169.
[http://dx.doi.org/10.1021/cr900184e] [PMID: 20078038]
(d)Yeung, C.S.; Dong, V.M. Chem. Rev., 2011, 111(3), 1215-1292.
[http://dx.doi.org/10.1021/cr100280d] [PMID: 21391561]
[8]
(a)Li, Y.; Geng, J.; Liu, Y.; Yu, S.; Zhao, G. ChemMedChem, 2013, 8(1), 27-41.
[http://dx.doi.org/10.1002/cmdc.201200355] [PMID: 23208773]
(b)Matysiak, J. Eur. J. Med. Chem., 2007, 42(7), 940-947.
[http://dx.doi.org/10.1016/j.ejmech.2006.12.033] [PMID: 17320247]
(c)He, G.S.; Tan, L-S.; Zheng, Q.; Prasad, P.N. Chem. Rev., 2008, 108(4), 1245-1330.
[http://dx.doi.org/10.1021/cr050054x] [PMID: 18361528]
(d)Cai, X-H.; Yang, M-H. Lett. Org. Chem., 2019, 16, 1-23.
[9]
(a)Oksuzoglu, E.; Tekiner-Gulbas, B.; Alper, S.; Temiz-Arpaci, O.; Ertan, T.; Yildiz, I.; Diril, N.; Sener-Aki, E.; Yalcin, I. J. Enzyme Inhib. Med. Chem., 2008, 23(1), 37-42.
[http://dx.doi.org/10.1080/14756360701342516] [PMID: 18341251]
(b)Oksuzoglu, E.; Temiz-Arpaci, O.; Tekiner-Gulbas, B.; Eroglu, H.; Sen, G.; Alper, S.; Yildiz, I.; Diril, N.; Aki-Sener, E.; Yalcin, I. Med. Chem. Res., 2007, 16, 1-14.
[http://dx.doi.org/10.1007/s00044-007-9005-z]
(c)Potashman, M.H.; Bready, J.; Coxon, A.; DeMelfi, T.M., Jr; DiPietro, L.; Doerr, N.; Elbaum, D.; Estrada, J.; Gallant, P.; Germain, J.; Gu, Y.; Harmange, J-C.; Kaufman, S.A.; Kendall, R.; Kim, J.L.; Kumar, G.N.; Long, A.M.; Neervannan, S.; Patel, V.F.; Polverino, A.; Rose, P.; Plas, Sv.; Whittington, D.; Zanon, R.; Zhao, H. J. Med. Chem., 2007, 50(18), 4351-4373.
[http://dx.doi.org/10.1021/jm070034i] [PMID: 17696416]
(d)Huang, S.T.; Hsei, I.J.; Chen, C. Bioorg. Med. Chem., 2006, 14(17), 6106-6119.
[http://dx.doi.org/10.1016/j.bmc.2006.05.007] [PMID: 16714116]
[10]
(a)Yang, C.C.; Tian, Y.; Chen, C.Y.; Jen, A.K.Y.; Chen, W.C. Macromol. Rapid Commun., 2007, 28, 894-899.
[http://dx.doi.org/10.1002/marc.200600869]
(b)Ogura, T.; Yamaguchi, K.; Shibasaki, Y.; Ueda, M. Polym. J., 2007, 39, 245-251.
[http://dx.doi.org/10.1295/polymj.PJ2006174]
(c)Ogoshi, T.; Miyake, J.; Chujo, Y. Macromolecules, 2005, 38, 4425-4431.
[http://dx.doi.org/10.1021/ma047320d]
[11]
(a)Riadi, Y.; Mamouni, R.; Azzalou, R.; El Haddad, M.; Routier, S.; Guillaumet, G.; Lazar, S. Tetrahedron Lett., 2011, 52, 3492-3495.
[http://dx.doi.org/10.1016/j.tetlet.2011.04.121]
(b)Wang, H.; Wang, L.; Shang, J.; Li, X.; Wang, H.; Gui, J.; Lei, A. Chem. Commun. (Camb.), 2012, 48(1), 76-78.
[http://dx.doi.org/10.1039/C1CC16184A] [PMID: 22089808]
(c)Bonnamour, J.; Bolm, C. Org. Lett., 2008, 10(13), 2665-2667.
[http://dx.doi.org/10.1021/ol800744y] [PMID: 18507387]
(d)Tian, Q.; Luo, W.; Gan, Z.; Li, D.; Dai, Z.; Wang, H.; Wang, X.; Yuan, J. Molecules, 2019, 24, 174-186.
[http://dx.doi.org/10.3390/molecules24010174]
(e)Mogharabi-Manzari, M.; Kiani, M.; Aryanejad, S.; Imanparast, S.; Amini, M.; Faramarzi, M.A. Adv. Synth. Catal., 2018, 360, 3563-3571.
[http://dx.doi.org/10.1002/adsc.201800459]
(f)Soselia, M.; Geibel, I.; Zurabishvili, D.; Samsoniya, S.J. Chem, 2018, 55, 447-455.
[12]
Hu, W-Y.; Wang, P-P.; Zhang, S-L. Synthesis, 2015, 47, 42-48.
[13]
(a)Guchhait, S.K.; Kashyap, M.; Saraf, S. Synthesis, 2010, 7, 1166-1170.
[http://dx.doi.org/10.1055/s-0029-1219234]
(b)Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M. ChemCatChem, 2010, 2, 1403-1406.
[http://dx.doi.org/10.1002/cctc.201000223]
(c)Ranjit, S.; Liu, X. Chemistry, 2011, 17(4), 1105-1108.
[http://dx.doi.org/10.1002/chem.201002787] [PMID: 21243674]
(d)Naikwade, A.; Jagadale, M.; Kale, D.; Gajare, S.; Rashinkar, G. Catal. Lett., 2018, 148, 3178-3192.
[http://dx.doi.org/10.1007/s10562-018-2514-1]
[14]
Clark, J.H. Curr. Opin. Green Sustain. Chem., 2017, 8, 10-13.
[http://dx.doi.org/10.1016/j.cogsc.2017.07.008]
[15]
(a)Shukla, A.; Zhang, Y.H.; Dubey, P.; Margrave, J.L.; Shukla, S.S. J. Hazard. Mater., 2002, 95(1-2), 137-152.
[http://dx.doi.org/10.1016/S0304-3894(02)00089-4] [PMID: 12409244]
(b)Pekkuz, H.; Uzun, I.; Güzel, F. Bioresour. Technol., 2008, 99(6), 2009-2017.
[http://dx.doi.org/10.1016/j.biortech.2007.03.014] [PMID: 17470390]
[16]
(a)Sadeghi, B.; Zarepour, I.J. Chem, 2015, 5, 305-311.
(b)Sadeghi, B.; Bouslik, M.; Shishehbore, M.R.J. Iran. Chem. Soc., 2015, 12, 1801-1808.
[http://dx.doi.org/10.1007/s13738-015-0655-3]
(c)Tahanpesar, E.; Sarami, L. Russ. J. Gen. Chem., 2015, 85, 2135-2140.
[http://dx.doi.org/10.1134/S1070363215090182]
(d)Karhale, S.; Patil, M.; Rashinkar, G.; Helavi, V. Res. Chem. Intermed., 2017, 43, 7073-7086.
[http://dx.doi.org/10.1007/s11164-017-3059-4]
[17]
(a)Kurane, R.; Jadhav, J.; Khanapure, S.; Salunkhe, R.; Rashinkar, G. Green Chem., 2013, 15, 1849-1856.
[http://dx.doi.org/10.1039/c3gc40592c]
(b)Jagadale, M.; Kale, D.; Salunkhe, R.; Rajmane, M.; Rashinkar, G. J. Mol. Liq., 2018, 265, 525-535.
[http://dx.doi.org/10.1016/j.molliq.2018.06.039]
[18]
Nirmala, M.; Saranya, G.; Viswanathamurthi, P.; Bertani, R.; Sgarbossa, P.; Malecki, J.G. J. Organomet. Chem., 2017, 831, 1-10.
[http://dx.doi.org/10.1016/j.jorganchem.2016.12.029]
[19]
Kolel-Veetil, M.K.; Gamache, R.M.; Bernstein, N.L.; Goswami, R.; Qadri, S.B.; Fears, K.P.; Miller, J.B.; Glaser, E.R.; Keller, T.M. J. Mater. Chem. C Mater. Opt. Electron. Devices, 2015, 3, 11705-11716.
[http://dx.doi.org/10.1039/C5TC02956B]
[20]
Wang, X. Carbohydr. Polym., 2014, 114, 476-483.
[http://dx.doi.org/10.1016/j.carbpol.2014.08.030] [PMID: 25263916]
[21]
Ai, W.; Liu, J.Q.; Du, Z.Z.; Liu, X.X.; Shang, J.Z.; Yi, M.D.; Xie, L.H.; Zhang, J.J.; Lin, H.F.; Yu, T.; Huang, W. RSC Advances, 2013, 3, 45-49.
[http://dx.doi.org/10.1039/C2RA22009A]
[22]
Hurst, E.C.; Wilson, K.; Fairlamb, I.J.S.; Chechik, V. New J. Chem., 2009, 33, 1837-1840.
[http://dx.doi.org/10.1039/b905559b]
[23]
Ji, L. J. Mater. Chem., 2012, 22, 15853-15862.
[http://dx.doi.org/10.1039/c2jm32896h]
[24]
Hao, J.; Li, Y.; Liao, R.; Liu, G.; Liao, Q.; Tang, C. Polymers (Basel), 2017, 9, 502-521.
[http://dx.doi.org/10.3390/polym9100502]
[25]
Lu, Q.; Yu, H.; Fu, Y. J. Am. Chem. Soc., 2014, 136(23), 8252-8260.
[http://
[1]
(a)Ofele, K.J. J. Organomet. Chem., 1968, 12, 42-43.
[http://dx.doi.org/10.1016/S0022-328X(00)88691-X]]
(b)Wanzlic, H.W.; Schonherr, H.J. Angew. Chem. Int. Ed. Engl., 1968, 7, 141-142.
[http://dx.doi.org/10.1002/anie.196801412]]
(c)Díez-González, S.; Marion, N.; Nolan, S.P. Chem. Rev., 2009, 109(8), 3612-3676.
[http://dx.doi.org/10.1021/cr900074m] [PMID: 19588961]
(d)Fortman, G.C.; Nolan, S.P. J. Curr. Org. Chem., 2014, 18, 700-718.
[2]
(a)Velazquez, H.D.; Verpoort, F. Chem. Soc. Rev., 2012, 41(21), 7032-7060.
[http://dx.doi.org/10.1039/c2cs35102a] [PMID: 22842861]
(b)Díez-González, S.; Marion, N.; Nolan, S.P. Chem. Rev., 2009, 109(8), 3612-3676.
[http://dx.doi.org/10.1021/cr900074m] [PMID: 19588961]
(c)Cai, X-H.; Xie, B. Mini Rev. Org. Chem., 2018, 15, 248-260.
[http://dx.doi.org/10.2174/1570193X14666171018150710]
[3]
(a)Nelson, D.J.; Nolan, S.P. Chem. Soc. Rev., 2013, 42(16), 6723-6753.
[http://dx.doi.org/10.1039/c3cs60146c] [PMID: 23788114]
(b)Díez-González, S.; Nolan, S.P. Coord. Chem. Rev., 2007, 251, 874-883.
[http://dx.doi.org/10.1016/j.ccr.2006.10.004]]
(c)Würtz, S.; Glorius, F. Acc. Chem. Res., 2008, 41(11), 1523-1533.
[http://dx.doi.org/10.1021/ar8000876] [PMID: 18720995]
(d)Valente, C.; Çalimsiz, S.; Hoi, K.H.; Mallik, D.; Sayah, M.; Organ, M.G. Angew. Chem. Int. Ed., 2012, 51, 3314-3332.
[http://dx.doi.org/10.1002/anie.201106131]
[4]
(a)Cavallo, L.; Correa, A.; Costabile, C.; Jacobsen, H. J. Organomet. Chem., 2005, 690, 5407-5413.
[http://dx.doi.org/10.1016/j.jorganchem.2005.07.012]]
(b)Turkmen, H.; Cetinkaya, B. J. Organomet. Chem., 2006, 691, 3749-3759.
[http://dx.doi.org/10.1016/j.jorganchem.2006.05.020]
[5]
(a)Chemistry, 2015, 21, 12291-12294.
(b)Cazin, C.S.J. J. Catal. Sci. Tech., 2013, 3, 2161-2181.
[6]
(a)Wang, Z.; Yu, Y.; Zhang, Y.X.; Li, S.Z.; Qian, H.; Lin, Z.Y. Green Chem., 2015, 17, 413-420.
[http://dx.doi.org/10.1039/C4GC00574K]
(b)Kim, J-H.; Kim, J-W.; Shokouhimehr, M.; Lee, Y-S. J. Org. Chem., 2005, 70(17), 6714-6720.
[http://dx.doi.org/10.1021/jo050721m] [PMID: 16095291]
(c)Qiu, H.; Sarkar, S.M.; Lee, D-H.; Jin, M-J. Green Chem., 2008, 10, 37-40.
[http://dx.doi.org/10.1039/B712624G]
(d)Zhou, H.; Zhang, Q-Y.; Lu, X-B. RSC Advances, 2016, 6, 44995-45000.
[http://dx.doi.org/10.1039/C6RA07786B]
(e)Shang, N.; Gao, S.; Feng, C.; Zhang, H.; Wang, C.; Wang, Z. RSC Adv., 2013, 21863-21868.
[7]
(a)Crabtree, R.H.; Lei, A. Chem. Rev., 2017, 117(13), 8481-8482.
[http://dx.doi.org/10.1021/acs.chemrev.7b00307] [PMID: 28697603]
(b)Gensch, T.; Hopkinson, M.N.; Glorius, F. J.Chem. Soc. Rev., 2016, 45, 2900-2936.
[http://dx.doi.org/10.1039/C6CS00075D]
(c)Lyons, T.W.; Sanford, M.S. Chem. Rev., 2010, 110(2), 1147-1169.
[http://dx.doi.org/10.1021/cr900184e] [PMID: 20078038]
(d)Yeung, C.S.; Dong, V.M. Chem. Rev., 2011, 111(3), 1215-1292.
[http://dx.doi.org/10.1021/cr100280d] [PMID: 21391561]
[8]
(a)Li, Y.; Geng, J.; Liu, Y.; Yu, S.; Zhao, G. ChemMedChem, 2013, 8(1), 27-41.
[http://dx.doi.org/10.1002/cmdc.201200355] [PMID: 23208773]
(b)Matysiak, J. Eur. J. Med. Chem., 2007, 42(7), 940-947.
[http://dx.doi.org/10.1016/j.ejmech.2006.12.033] [PMID: 17320247]
(c)He, G.S.; Tan, L-S.; Zheng, Q.; Prasad, P.N. Chem. Rev., 2008, 108(4), 1245-1330.
[http://dx.doi.org/10.1021/cr050054x] [PMID: 18361528]
(d)Cai, X-H.; Yang, M-H. Lett. Org. Chem., 2019, 16, 1-23.
[9]
(a)Oksuzoglu, E.; Tekiner-Gulbas, B.; Alper, S.; Temiz-Arpaci, O.; Ertan, T.; Yildiz, I.; Diril, N.; Sener-Aki, E.; Yalcin, I. J. Enzyme Inhib. Med. Chem., 2008, 23(1), 37-42.
[http://dx.doi.org/10.1080/14756360701342516] [PMID: 18341251]
(b)Oksuzoglu, E.; Temiz-Arpaci, O.; Tekiner-Gulbas, B.; Eroglu, H.; Sen, G.; Alper, S.; Yildiz, I.; Diril, N.; Aki-Sener, E.; Yalcin, I. Med. Chem. Res., 2007, 16, 1-14.
[http://dx.doi.org/10.1007/s00044-007-9005-z]
(c)Potashman, M.H.; Bready, J.; Coxon, A.; DeMelfi, T.M., Jr; DiPietro, L.; Doerr, N.; Elbaum, D.; Estrada, J.; Gallant, P.; Germain, J.; Gu, Y.; Harmange, J-C.; Kaufman, S.A.; Kendall, R.; Kim, J.L.; Kumar, G.N.; Long, A.M.; Neervannan, S.; Patel, V.F.; Polverino, A.; Rose, P.; Plas, Sv.; Whittington, D.; Zanon, R.; Zhao, H. J. Med. Chem., 2007, 50(18), 4351-4373.
[http://dx.doi.org/10.1021/jm070034i] [PMID: 17696416]
(d)Huang, S.T.; Hsei, I.J.; Chen, C. Bioorg. Med. Chem., 2006, 14(17), 6106-6119.
[http://dx.doi.org/10.1016/j.bmc.2006.05.007] [PMID: 16714116]
[10]
(a)Yang, C.C.; Tian, Y.; Chen, C.Y.; Jen, A.K.Y.; Chen, W.C. Macromol. Rapid Commun., 2007, 28, 894-899.
[http://dx.doi.org/10.1002/marc.200600869]
(b)Ogura, T.; Yamaguchi, K.; Shibasaki, Y.; Ueda, M. Polym. J., 2007, 39, 245-251.
[http://dx.doi.org/10.1295/polymj.PJ2006174]
(c)Ogoshi, T.; Miyake, J.; Chujo, Y. Macromolecules, 2005, 38, 4425-4431.
[http://dx.doi.org/10.1021/ma047320d]
[11]
(a)Riadi, Y.; Mamouni, R.; Azzalou, R.; El Haddad, M.; Routier, S.; Guillaumet, G.; Lazar, S. Tetrahedron Lett., 2011, 52, 3492-3495.
[http://dx.doi.org/10.1016/j.tetlet.2011.04.121]
(b)Wang, H.; Wang, L.; Shang, J.; Li, X.; Wang, H.; Gui, J.; Lei, A. Chem. Commun. (Camb.), 2012, 48(1), 76-78.
[http://dx.doi.org/10.1039/C1CC16184A] [PMID: 22089808]
(c)Bonnamour, J.; Bolm, C. Org. Lett., 2008, 10(13), 2665-2667.
[http://dx.doi.org/10.1021/ol800744y] [PMID: 18507387]
(d)Tian, Q.; Luo, W.; Gan, Z.; Li, D.; Dai, Z.; Wang, H.; Wang, X.; Yuan, J. Molecules, 2019, 24, 174-186.
[http://dx.doi.org/10.3390/molecules24010174]
(e)Mogharabi-Manzari, M.; Kiani, M.; Aryanejad, S.; Imanparast, S.; Amini, M.; Faramarzi, M.A. Adv. Synth. Catal., 2018, 360, 3563-3571.
[http://dx.doi.org/10.1002/adsc.201800459]
(f)Soselia, M.; Geibel, I.; Zurabishvili, D.; Samsoniya, S.J. Chem, 2018, 55, 447-455.
[12]
Hu, W-Y.; Wang, P-P.; Zhang, S-L. Synthesis, 2015, 47, 42-48.
[13]
(a)Guchhait, S.K.; Kashyap, M.; Saraf, S. Synthesis, 2010, 7, 1166-1170.
[http://dx.doi.org/10.1055/s-0029-1219234]
(b)Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M. ChemCatChem, 2010, 2, 1403-1406.
[http://dx.doi.org/10.1002/cctc.201000223]
(c)Ranjit, S.; Liu, X. Chemistry, 2011, 17(4), 1105-1108.
[http://dx.doi.org/10.1002/chem.201002787] [PMID: 21243674]
(d)Naikwade, A.; Jagadale, M.; Kale, D.; Gajare, S.; Rashinkar, G. Catal. Lett., 2018, 148, 3178-3192.
[http://dx.doi.org/10.1007/s10562-018-2514-1]
[14]
Clark, J.H. Curr. Opin. Green Sustain. Chem., 2017, 8, 10-13.
[http://dx.doi.org/10.1016/j.cogsc.2017.07.008]
[15]
(a)Shukla, A.; Zhang, Y.H.; Dubey, P.; Margrave, J.L.; Shukla, S.S. J. Hazard. Mater., 2002, 95(1-2), 137-152.
[http://dx.doi.org/10.1016/S0304-3894(02)00089-4] [PMID: 12409244]
(b)Pekkuz, H.; Uzun, I.; Güzel, F. Bioresour. Technol., 2008, 99(6), 2009-2017.
[http://dx.doi.org/10.1016/j.biortech.2007.03.014] [PMID: 17470390]
[16]
(a)Sadeghi, B.; Zarepour, I.J. Chem, 2015, 5, 305-311.
(b)Sadeghi, B.; Bouslik, M.; Shishehbore, M.R.J. Iran. Chem. Soc., 2015, 12, 1801-1808.
[http://dx.doi.org/10.1007/s13738-015-0655-3]
(c)Tahanpesar, E.; Sarami, L. Russ. J. Gen. Chem., 2015, 85, 2135-2140.
[http://dx.doi.org/10.1134/S1070363215090182]
(d)Karhale, S.; Patil, M.; Rashinkar, G.; Helavi, V. Res. Chem. Intermed., 2017, 43, 7073-7086.
[http://dx.doi.org/10.1007/s11164-017-3059-4]
[17]
(a)Kurane, R.; Jadhav, J.; Khanapure, S.; Salunkhe, R.; Rashinkar, G. Green Chem., 2013, 15, 1849-1856.
[http://dx.doi.org/10.1039/c3gc40592c]
(b)Jagadale, M.; Kale, D.; Salunkhe, R.; Rajmane, M.; Rashinkar, G. J. Mol. Liq., 2018, 265, 525-535.
[http://dx.doi.org/10.1016/j.molliq.2018.06.039]
[18]
Nirmala, M.; Saranya, G.; Viswanathamurthi, P.; Bertani, R.; Sgarbossa, P.; Malecki, J.G. J. Organomet. Chem., 2017, 831, 1-10.
[http://dx.doi.org/10.1016/j.jorganchem.2016.12.029]
[19]
Kolel-Veetil, M.K.; Gamache, R.M.; Bernstein, N.L.; Goswami, R.; Qadri, S.B.; Fears, K.P.; Miller, J.B.; Glaser, E.R.; Keller, T.M. J. Mater. Chem. C Mater. Opt. Electron. Devices, 2015, 3, 11705-11716.
[http://dx.doi.org/10.1039/C5TC02956B]
[20]
Wang, X. Carbohydr. Polym., 2014, 114, 476-483.
[http://dx.doi.org/10.1016/j.carbpol.2014.08.030] [PMID: 25263916]
[21]
Ai, W.; Liu, J.Q.; Du, Z.Z.; Liu, X.X.; Shang, J.Z.; Yi, M.D.; Xie, L.H.; Zhang, J.J.; Lin, H.F.; Yu, T.; Huang, W. RSC Advances, 2013, 3, 45-49.
[http://dx.doi.org/10.1039/C2RA22009A]
[22]
Hurst, E.C.; Wilson, K.; Fairlamb, I.J.S.; Chechik, V. New J. Chem., 2009, 33, 1837-1840.
[http://dx.doi.org/10.1039/b905559b]
[23]
Ji, L. J. Mater. Chem., 2012, 22, 15853-15862.
[http://dx.doi.org/10.1039/c2jm32896h]
[24]
Hao, J.; Li, Y.; Liao, R.; Liu, G.; Liao, Q.; Tang, C. Polymers (Basel), 2017, 9, 502-521.
[http://dx.doi.org/10.3390/polym9100502]
[25]
Lu, Q.; Yu, H.; Fu, Y. J. Am. Chem. Soc., 2014, 136(23), 8252-8260.
[http://dx.doi.org/10.1021/ja4127455] [PMID: 24823646]
dx.doi.org/10.1021/ja4127455] [PMID: 24823646]

Rights & Permissions Print Cite
Article Metrics
7
© 2024 Bentham Science Publishers | Privacy Policy