Abstract
Stereochemically inert, positively charged chiral octahedral complexes of CoIII and CrIII were used as catalysts for asymmetric oxidative coupling of 2-naphthol. The reaction product 1,1´-bi-2-naphthol was produced with a yield of up to 74% and enantiomeric excess of up to 22%. The reduction and oxidation potentials of a series of CoIII and CrIII cationic complexes were measured.
Similar content being viewed by others
References
P. Kočovský, Š. Vyskočil, M. Smrčina, Chem. Rev., 2003, 103, 3213.
S. J. Connon, Angew. Chem., Int. Ed., 2006, 45, 3909.
T. Akiyama, Chem. Rev., 2007, 107, 5744.
M. Smrčina, J. Poláková, Š. Vyskočil, P. Kočovský, J. Org. Chem., 1993, 58, 4534.
M. Nakajima, K. Kanayama, I. Miyashi, S. Hashimoto, Tetrahedron Lett., 1995, 36, 9519.
X. Li, J. Yang, M. C. Kozlowski, Org. Lett., 2001, 3, 1137.
J. Gao, J. H. Reibenspies, A. E. Martell, Angew. Chem., Int. Ed., 2003, 42, 6008.
T. Temma, S. Habaue, Tetrahedron Lett., 2005, 46, 5655.
C.-Y. Chu, D.-R. Hwang, S.-K. Wang, B.-J. Uang, Chem. Commun., 2001, 980.
S.-W. Hon, C.-H. Li, J.-H. Kuo, N. B. Barhate, Y.-H. Liu, Y. Wang, C.-T. Chen, Org. Lett., 2001, 3, 869.
Z. Luo, Q. Liu, L. Gong, X. Cui, A. Mi, Y. Jiang, Angew. Chem., Int. Ed., 2002, 41, 4532.
Q.-X. Guo, Z.-J. Wu, Z.-B. Luo, Q.-Z. Liu, J.-L. Ye, S.-W. Luo, L.-F. Cun, L.-Z. Gong, J. Am. Chem. Soc., 2007, 129, 13927.
H. Somei, Y. Asano, T. Yoshida, S. Takizawa, H. Yamataka, H. Sasai, Tetrahedron Lett., 2004, 45, 1841.
H. Egami, T. Katsuki, J. Am. Chem. Soc., 2009, 131, 6082.
H. Egami, K. Matsumoto, T. Oguma, T. Kunisu, T. Katsuki, J. Am. Chem. Soc., 2010, 132, 13633.
Yu. N. Belokon, V. A. Larionov, A. F. Mkrtchyan, V. N. Khrustalev, A. Nijland, A. S. Saghyan, I. A. Godovikov, A. S. Peregudov, K. K. Babievsky, N. S. Ikonnikov, V. I. Maleev, Russ. Chem. Bull. (Int. Ed.), 2012, 61, 2252 [Izv. Akad. Nauk, Ser. Khim., 2012, 2231].
Yu. N. Belokon, V. I. Maleev, M. North, V. A. Larionov, T. F. Savelýeva, A. Nijland, Y. V. Nelyubina, ACS Catal., 2013, 3, 1951.
V. I. Maleev, M. North, V. A. Larionov, I. V. Fedyanin, T. F. Savelýeva, M. A. Moscalenko, A. F. Smolyakov, Yu. N. Belokon, Adv. Synth. Catal., 2014, 356, 1803.
V. A. Larionov, PhD Thesis (Chem.), A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Moscow, 2014, 135 pp. (in Russian).
L. Gong, L.-A. Chen, E. Meggers, Angew. Chem., Int. Ed., 2014, 53, 10868.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0685—0688, March, 2016.
Rights and permissions
About this article
Cite this article
Larionov, V.A., Peregudova, S.M., Maleev, V.I. et al. A novel type of catalysts for asymmetric oxidative coupling of 2-naphthol. Russ Chem Bull 65, 685–688 (2016). https://doi.org/10.1007/s11172-016-1356-5
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-016-1356-5