Catalytic and mechanistic studies into the epoxidation of styrenes using manganese complexes of structurally similar polyamine ligands
作者： Gennadiy Ilyashenko , Giorgio De Faveri , Thomas Follier , Rawan Al-Safadi , Majid Motevalli
DOI: 10.1039/C3OB42274G
关键词:
摘要: Two structurally similar polyamine ligands (7 and 8) have been prepared, which differ only by the presence of either a secondary or tertiary nitrogen donor within their N5 set. The ligands, in combination with iron manganese salts, screened for efficacy as catalysts epoxidation styrene, using both hydrogen peroxide peracetic acid oxidants. Clear differences activity between two systems were observed, 7 proving most effective MnSO4 H2O2, whereas ligand 8 proved to be Mn(OTf)2, MnCl2 Mn(ClO4)2 oxidant. A Hammett analysis initial rate kinetics optimal systems, combined UV-vis spectroscopy, indicates that small structural elicit profound changes nature active species formed.
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sci-hub.se 参考文章(48)
Iwao Ojima, Catalytic asymmetric synthesis ,(1993)
Tsutomu Katsuki, K. Barry Sharpless, First practical method for asymmetric epoxidation Journal of the American Chemical Society. ,vol. 102, pp. 5974- 5976 ,(1981) , 10.1021/JA00538A077
Eoghan M. McGarrigle, Declan G. Gilheany, Chromium− and Manganese−salen Promoted Epoxidation of Alkenes Chemical Reviews. ,vol. 105, pp. 1563- 1602 ,(2005) , 10.1021/CR0306945
Xiujuan Wu, Mi Sook Seo, Katherine M. Davis, Yong-Min Lee, Junying Chen, Kyung-Bin Cho, Yulia N. Pushkar, Wonwoo Nam, A Highly Reactive Mononuclear Non-Heme Manganese(IV)–Oxo Complex That Can Activate the Strong C–H Bonds of Alkanes Journal of the American Chemical Society. ,vol. 133, pp. 20088- 20091 ,(2011) , 10.1021/JA208523U
Tsutomu Katsuki, Catalytic asymmetric oxidations using optically active (salen)manganese(III) complexes as catalysts Coordination Chemistry Reviews. ,vol. 140, pp. 189- 214 ,(1995) , 10.1016/0010-8545(94)01124-T
Henri-Jean Cristau, Pascal P. Cellier, Samy Hamada, Jean-Francis Spindler, Marc Taillefer, A General and Mild Ullmann-Type Synthesis of Diaryl Ethers Organic Letters. ,vol. 6, pp. 913- 916 ,(2004) , 10.1021/OL036290G
Georgiy B. Shul'pin, C–H functionalization: thoroughly tuning ligands at a metal ion, a chemist can greatly enhance catalyst's activity and selectivity Dalton Transactions. ,vol. 42, pp. 12794- 12818 ,(2013) , 10.1039/C3DT51004B
Wonchoul Park, Mi Hee Shin, Jin Ho Chung, Jaejoon Park, Myoung Soo Lah, Dongyeol Lim, Synthesis and manganese complexes of pentagonal bipyramidal ligands: N,N′-disubstituted pentaaza macrocycles Tetrahedron Letters. ,vol. 47, pp. 8841- 8845 ,(2006) , 10.1016/J.TETLET.2006.10.063
Olaf Cussó, Isaac Garcia-Bosch, Xavi Ribas, Julio Lloret-Fillol, Miquel Costas, Asymmetric epoxidation with H2O2 by manipulating the electronic properties of non-heme iron catalysts. Journal of the American Chemical Society. ,vol. 135, pp. 14871- 14878 ,(2013) , 10.1021/JA4078446
Tsutomu Katsuki, Chiral Metallosalen Complexes: Structures and Catalyst Tuning for Asymmetric Epoxidation and Cyclopropanation Advanced Synthesis & Catalysis. ,vol. 344, pp. 131- 147 ,(2002) , 10.1002/1615-4169(200202)344:2<131::AID-ADSC131>3.0.CO;2-T