Abstract
The synthesis and characterization of substituted ONNO-donor salen-type Schiff base complexes of general formula [MIII(L)Cl] (L = Schiff base ligand, M = Fe, Co) is reported. The complexes have been applied as catalysts for the coupling of carbon dioxide and styrene oxide in the presence of tetrabutylammonium bromide as a co-catalyst. The reactions were carried out under relatively low-pressure and solvent-free conditions. The effects of the metal center, ligands, and various substituents on the peripheral sites of the ligand on the coupling reaction were investigated. The catalyst systems were found to be selective for the coupling of CO2 and styrene oxide, resulting in cyclic styrene carbonate. The cobalt(III) complex with no substituents on the ligand showed higher activity (TON = 1297) than the corresponding iron(III) complex (TON = 814); however, the iron(III)-based catalysts bearing electron-withdrawing substituents on the salen ligands (NEt3, TON = 1732) showed the highest catalytic activity under similar reaction conditions. The activity of one of the cobalt(III) complexes toward the coupling of 1-butene oxide, cyclohexene oxide and propylene oxide with CO2 was evaluated, revealing a notable activity for the coupling of 1-butene oxide.
Similar content being viewed by others
References
Musie G, Wei M, Subramaniam B, Busch DH (2001) Coord Chem Rev 219:789
Leitner W (1996) Coord Chem Rev 153:257
Leitner W (1995) Angew Chem 107:2391
Shi M, Shen YM (2003) Curr Org Chem 7:737
Yin X, Moss JR (1999) Coord Chem Rev 181:27
Gibson DH (1996) Chem Rev 96:2063
Inoue S (1976) ChemTech 6:588
Darensbourg DJ, Holtcamp MW (1996) Coord Chem Rev 153:155
Beckman EJ (1999) Science 283:946
Darensbourg DJ (2007) Chem Rev 107:2388
Klaus S, Lehenmeier MW, Anderson CE, Rieger B (2011) Coord Chem Rev 255:1460
Coates GW, Moore DR (2004) Angew Chem Int Ed 43:6618
Kember MR, Buchard A, Williams CK (2011) Chem Commun 47:141
Decortes A, Castilla AM, Kleij AW (2010) Angew Chem Int Ed 49:9822
Thorat SD, Phillips PJ, Semenov V, Gakh A (2003) J Appl Polym Sci 89:1163
Liu B, Chen L, Zhang M, Yu A (2002) Macromol Rapid Commun 23:881
Wang SJ, Du LC, Zhao XS, Meng YZ, Tjong SC (2002) J Appl Polym Sci 85:2327
Wu X-M, Sun W, Xin J-Y, Xia C-G (2008) World J Microbiol Biotechnol 24:2421
Srivastava R, Srinivas D, Ratnasamy P (2006) J Catal 241:34
Shaikh A-AG, Sivaram S (1996) Chem Rev 96:951
Chen S-W, Kawthekar RB, Kim G-J (2007) Tetrahedron Lett 48:297
Paddock RL, Hiyama Y, Mckay JM, Nguyen ST (2004) Tetrahedron Lett 45:2023
Darensbourg DJ, Mackiewicz RM (2005) J Am Chem Soc 127:14026
Cohen CT, Chu T, Coates GW (2005) J Am Chem Soc 127:10869
Bu Z, Wang Z, Yang L, Cao S (2011) App Organometal Chem 24:813
Decortes A, Belmonte MM, Benet-Buchholz J, Kleij AW (2010) Chem Commun 46:4580
Fujita S-I, Nishiura M, Arai M (2010) Catal Lett 135:263
North M, Pasquale R (2009) Angew Chem Int Ed 48:2946
Luinstra GA, Haas GR, Molnar F, Bernhart V, Eberhardt R, Rieger B (2005) Chem Eur J 11:6298
Jing H, Edulji SK, Gibbs JM, Stern CL, Zhou H, Nguyen ST (2004) Inorg Chem 43:4315
Kember MR, White AJP, Williams CK (2010) Macromolecules 43:2291
Buchard A, Kember MR, Sandeman K, Williams CK (2011) Chem Commun 47:212–214
Edulji SK, Nguyen ST (2004) Pure Appl Chem 76:645
Dengler JE, Lehenmeier MW, Klaus S, Anderson CE, Herdtweck E, Rieger B (2011) Eur J Inorg Chem 336–343
Al-Qaisi F, Genjang N, Nieger M, Repo T (2016) Inorg Chim Acta 442:81
Sunjuk M, Abu-Surrah AS, Al-Ramahi E, Qaroush AK, Saleh A (2013) Transition Met Chem 38:253
Cozzi P (2004) Chem Soc Rev 33:410
Yliheikkilä K, Lappalainen K, Castro PM, Ibrahim K, Abu-Surrah AS, Leskelä M, Repo T (2006) Eur Polym J 42:92
Lu X-B, Shi L, Wang Y-M, Zhang R, Zhang Y-J, Peng X-J, Zhan Z-C, Li B (2006) J Am Chem Soc 128:1664
Nielsen LPC, Stevenson CP, Blackmond DG, Jacobsen EN (2004) J Am Chem Soc 126:1360
Lu X-B, Feng X-J, He R (2002) Appl Catal A 234:25
Wu G-P, Wei S-H, Lu X-B, Ren W-M, Darensbourg DJ (2010) Macromolecules 43:9202
Sibaouih A, Ryan P, Axenov KV, Sundberg MR, Leskelä M, Repo T (2009) J Mol Cat A: Chem 312:87
Acknowledgements
Financial support by the Hashemite University is gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Abu-Surrah, A.S., Abdel-Halim, H.M., Abu-Shehab, H.A.N. et al. Iron and cobalt salicylaldimine complexes as catalysts for epoxide and carbon dioxide coupling: effects of substituents on catalytic activity. Transit Met Chem 42, 117–122 (2017). https://doi.org/10.1007/s11243-016-0113-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11243-016-0113-9