Ketonization of methylene of bis(benzimidazol-2-yl)methane by molecular oxygen under the catalysis of cobalt(II) ion

作者: Hong-Chang Yao , Miao-Miao Li , Gao-Sheng Yang , Zhong-Jun Li , Yu Zhu

DOI: 10.1016/J.ICA.2007.04.042

关键词:

摘要: Abstract A cobalt(II) complex [Co((bnzim)2CO)Cl2] (1) (where (bnzim)2CO ; bis(benzimidazol-2-yl)methanone), was obtained by reacting chloride with bis(benzimidazol-2-yl)methane ((bnzim)2CH2) in CH3OH/CH3CN and characterized using EA, IR, XRD X-ray single crystal diffraction. The process of ketonization methylene (bnzim)2CH2 investigated spectroscopy electrochemistry method. experimental results reveal that there were new species forming the reaction system formation related to dissolving oxygen mixture. Oxygenation mechanism thus proposed, which atom transfer from a superoxo intermediate {((bnzim)2CH2)Co(III)–O–O } methylenic carbon (bnzim)2CH2, then goes O–O hemolytic cleavage hydrogen migration give [Co((bnzim)2CHOH)]2+. achieved after [Co((bnzim)2CHOH)]2+repeating process.

参考文章(10)
Katharina Isele, Vanessa Broughton, Craig J. Matthews, Alan F. Williams, G??rald Bernardinelli, Patrick Franz, Silvio Decurtins, 1,2-Bis(2-benzimidazolyl)-1,2-ethanediol, a chiral, tridentate, facially coordinating ligand Journal of the Chemical Society, Dalton Transactions. pp. 3899- 3905 ,(2002) , 10.1039/B203229E
Shiro Hikichi, Hidehito Komatsuzaki, Munetaka Akita, Yoshihiko Moro-oka, Aliphatic C−H Bond Oxygenation by the CoIIOOX Species with the Hindered Hydrotris(pyrazolyl)borate Ligand (X = Co(II), Alkyl, H) Journal of the American Chemical Society. ,vol. 120, pp. 4699- 4710 ,(1998) , 10.1021/JA9720523
Alessandro Abbotto, Antonio Facchetti, Silvia Bradamante, Giorgio A. Pagani, 8-Purinyl versus 2-Benzimidazolyl Carbanions: Charge Demands of the Heterocycles and Ligand Properties of the Bis(heteroaryl)methanes1 Journal of Organic Chemistry. ,vol. 63, pp. 436- 444 ,(1998) , 10.1021/JO970958L
Robert T. Stibrany, Donald N. Schulz, Smita Kacker, Abhimanyu O. Patil, Lisa S. Baugh, Steven P. Rucker, Stephen Zushma, Enock Berluche, Joseph A. Sissano, Polymerization and Copolymerization of Olefins and Acrylates by Bis(benzimidazole) Copper Catalysts Macromolecules. ,vol. 36, pp. 8584- 8586 ,(2003) , 10.1021/MA034548C
Sarah Elgafi, Leslie D Field, Barbara A Messerle, Peter Turner, Trevor W Hambley, Rhodium complexes containing bidentate imidazolyl ligands : synthesis and structure Journal of Organometallic Chemistry. ,vol. 588, pp. 69- 77 ,(1999) , 10.1016/S0022-328X(99)00347-2
Michael J. Samide, Dennis G. Peters, Electrochemical behavior of 3-chloro-2,4-pentanedione in the presence of cobalt salen Journal of Pharmaceutical and Biomedical Analysis. ,vol. 19, pp. 193- 203 ,(1999) , 10.1016/S0731-7085(98)00055-7
Trissa Joseph, S.B. Halligudi, C. Satyanarayan, Dhanashree P. Sawant, S. Gopinathan, Oxidation by molecular oxygen using zeolite encapsulated Co(II)saloph complexes Journal of Molecular Catalysis A-chemical. ,vol. 168, pp. 87- 97 ,(2001) , 10.1016/S1381-1169(00)00443-X
Marja K. Lajunen, Co(II) catalysed oxidation of α-pinene by molecular oxygen Journal of Molecular Catalysis A-chemical. ,vol. 169, pp. 223- 229 ,(2001) , 10.1016/S1381-1169(00)00560-4
Andrzej Sobkowiak, Donald T. Sawyer, Cobalt(II)-induced activation of dioxygen for the dehydrogenation of N-methylanilines and benzyl alcohol Journal of the American Chemical Society. ,vol. 113, pp. 9520- 9523 ,(1991) , 10.1021/JA00025A016
A. B. P Lever, Inorganic electronic spectroscopy Studies in Physical and Theoretical Chemistry. ,vol. 33, ,(1984)