European Journal of Chemistry 2010, 1(4), 360-367. doi:10.5155/eurjchem.1.4.360-367.221

Chiral Cu(II) salen complexes catalyzed aerobic oxidative biaryl coupling-probing the reaction by EPR


Subbaramanian Sabarinathan (1) , Gnanasambandam Vasuki (2,*) , Pillutla Sambasiva Rao (3)

(1) Department of Chemistry, Pondicherry University, Pudhucherry, IN-605 014, India
(2) Department of Chemistry, Pondicherry University, Pudhucherry, IN-605 014, India
(3) Department of Chemistry, Pondicherry University, Pudhucherry, IN-605 014, India
(*) Corresponding Author

Received: 24 Jul 2010, Accepted: 30 Sep 2010, Published: 22 Dec 2010

Abstract


Aerobic oxidative coupling of 2-naphthol to 1,1'-binaphthyl-2,2'-diol has been achieved using chiral/achiral copper salen complexes as catalyst. Moderate enantioselectivity was obtained for the reaction of 2-napthol with a coordinating substituent with a chiral salen complex. Unsubstituted 2-naphthol resulted in racemic 1,1'-binaphthyl-2,2'-diol only with all chiral complexes. Electron paramagnetic resonance spectroscopy has been used to understand the factors influencing the asymmetric induction.

1_4_360_367_800


Keywords


Biaryl coupling; Chiral copper salen complexes; Cross coupling; BINOL; Aerobic oxidation; EPR

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DOI: 10.5155/eurjchem.1.4.360-367.221

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References

[1]. Venkataramanan, N. S.; Kuppuraj, G.; Rajagopal, S. Coord. Chem. Rev. 2005, 249, 1249-1268.
doi:10.1016/j.ccr.2005.01.023

[2]. Baleizão, C; Garcia, H. Chem. Rev. 2006, 106, 3987-4043.
doi:10.1021/cr050973n
PMid:16967927

[3]. Achard, T. R. J.; Clutterbuck, L. A.; North, M. Synlett 2005, 12, 1828-1847.

[4]. Gupta, K. C.; Sutar A.K. Coord. Chem. Rev. 2008, 252, 1420-1450.
doi:10.1016/j.ccr.2007.09.005

[5]. Cozzi, P.G. Chem. Soc. Rev. 2004, 33, 410-421.
doi:10.1039/b307853c
PMid:15354222

[6]. Traa, Y; Murphy, D. M.; Farley, R. D.; Hutchings, G. J. Phys. Chem. Chem. Phys. 2001, 3, 1073-1080.
doi:10.1039/b010083h

[7]. Bolm, C; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M.; Schweiger, A.; Mitrikas, G.; Harmer J. J Am. Chem. Soc. 2003, 125, 6222-6227.
doi:10.1021/ja027870w
PMid:12785854

[8]. Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Stanoeva, T.; Chem, D.; Bertagnolli, H.; Feth, M.; Schweiger, A.; Mitrikas, G.; Harmer J. Chem. Eur J. 2006, 13, 1842-1850.
doi:10.1002/chem.200601086
PMid:17115464

[9]. Doorslaera, S. V.; Caretti, I.; Fallis, I. A.; Murphy, D. M. Coord. Chem. Rev. 2009, 253, 2116-2130.
doi:10.1016/j.ccr.2008.12.010

[10]. Zhu, H. B.; Dai, Z. Y.; Huang, W.; Cui, K.; Gou, S. H.; Zhu, C. J. Polyhedron 2004, 23, 1131-1137.
doi:10.1016/j.poly.2004.02.005

[11]. Liu, B.; Zhu, S.F.; Wang, L. X.; Zhou, Q. L. Tetrahedron: Asymmetry 2006, 17, 634-641.
doi:10.1016/j.tetasy.2006.02.010

[12]. Minato, D.; Arimoto, H.; Nagasue, Y.; Demizu, Y.; Onomura O. Tetrahedron 2008, 64, 6675-6683.
doi:10.1016/j.tet.2008.05.015

[13]. Bolm, C.; Schlingloff, G.; Bienewald, F. J. Mol. Catal. 1997, 117, 347-350.
doi:10.1016/S1381-1169(96)00359-7

[14]. Hoang, V. D. M.; Reddy, P. A. N.; Kim, T. J. Organometallics 2008, 27, 1026- 1027.
doi:10.1021/om700935m

[15]. Ginotra, S. K.; Singh, V. K. Org. Biomol. Chem. 2006, 4, 4370-4374.
doi:10.1039/b612423b

[16]. Mimmi, M. C.; Gullotti, M.; Santagostini, L.; Battaini, G.; Monzani, E.; Pagliarin, R.; Zoppellarod, G.; Casella, L. Dalton Trans 2004, 2192-2201.
doi:10.1039/b402539c
PMid:15249957

[17]. Ginotra, S. K.; Singh, V. K. Tetrahedron 2006, 62, 3573-3581.
doi:10.1016/j.tet.2006.01.093

[18]. Alamsetti, S. K.; Mannam, S.; Mutupandi, P.; Sekar, G. Chem. Eur. J. 2008, 15, 1086-1090.

[19]. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329-2363.
doi:10.1021/cr050523v
PMid:15941216

[20]. Pu, L. Chem. Rev. 1998, 98, 2405-2494.
doi:10.1021/cr970463w
PMid:11848968

[21]. Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155-3211.
doi:10.1021/cr020025b
PMid:12914495

[22]. Brunel, J. M. Chem. Rev 2005, 105, 857-897.
doi:10.1021/cr040079g
PMid:15755079

[23]. Smrčina, M.; Poláková, J.; Vyskočil, S.; Kočovský, P. J. Org. Chem. 1993, 58, 4534-4538.
doi:10.1021/jo00069a010

[24]. Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S. I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264-2271.
doi:10.1021/jo981808t

[25]. Li, X.; Hewgley, J. B.; Mulrooney, C. A.; Yang, J.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500-5511.
doi:10.1021/jo0340206
PMid:12839440

[26]. Noji, M.; Nakajima, M.; Koga, K. Tetrahedron letter 1994, 35, 7983-7984.

[27]. Larrow, J. F.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 1939-1942.
doi:10.1021/jo00086a062

[28]. Kalechits, G. V.; Osinovskii, A. G.; Matveenko, Y. V.; Ol’khovik, V. K. Russ. J. Appl. Chem. 2002, 75, 962-964.
doi:10.1023/A:1020397015477

[29]. Kureshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Patel, S. T.; Jasra, R. V. Tetrahedron: Asymmetry 2001, 12, 433-437.
doi:10.1016/S0957-4166(01)00057-X


How to cite


Sabarinathan, S.; Vasuki, G.; Rao, P. Eur. J. Chem. 2010, 1(4), 360-367. doi:10.5155/eurjchem.1.4.360-367.221
Sabarinathan, S.; Vasuki, G.; Rao, P. Chiral Cu(II) salen complexes catalyzed aerobic oxidative biaryl coupling-probing the reaction by EPR. Eur. J. Chem. 2010, 1(4), 360-367. doi:10.5155/eurjchem.1.4.360-367.221
Sabarinathan, S., Vasuki, G., & Rao, P. (2010). Chiral Cu(II) salen complexes catalyzed aerobic oxidative biaryl coupling-probing the reaction by EPR. European Journal of Chemistry, 1(4), 360-367. doi:10.5155/eurjchem.1.4.360-367.221
Sabarinathan, Subbaramanian, Gnanasambandam Vasuki, & Pillutla Sambasiva Rao. "Chiral Cu(II) salen complexes catalyzed aerobic oxidative biaryl coupling-probing the reaction by EPR." European Journal of Chemistry [Online], 1.4 (2010): 360-367. Web. 21 Sep. 2019
Sabarinathan, Subbaramanian, Vasuki, Gnanasambandam, AND Rao, Pillutla. "Chiral Cu(II) salen complexes catalyzed aerobic oxidative biaryl coupling-probing the reaction by EPR" European Journal of Chemistry [Online], Volume 1 Number 4 (22 December 2010)

DOI Link: https://doi.org/10.5155/eurjchem.1.4.360-367.221

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