Generation, Characterization, and Reactivity of a CuII-Alkylperoxide/Anilino Radical Complex: Insight into the O-O Bond Cleavage Mechanism

被引:30
作者
Paria, Sayantan [1 ]
Ohta, Takehiro [2 ]
Morimoto, Yuma [1 ]
Ogura, Takashi [2 ]
Sugimoto, Hideki [1 ]
Fujieda, Nobutaka [1 ]
Goto, Kei [3 ]
Asano, Kaori [4 ]
Suzuki, Takeyuki [4 ]
Itoh, Shinobu [1 ]
机构
[1] Osaka Univ, Grad Sch Engn, Dept Mat & Life Sci, Div Adv Sci & Biotechnol, Suita, Osaka 5650871, Japan
[2] Univ Hyogo, RSC UH LP Ctr, Grad Sch Life Sci, Picobiol Inst, Sayo, Hyogo 6795148, Japan
[3] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Chem, Meguro Ku, Tokyo 1528551, Japan
[4] Osaka Univ, ISIR, Comprehens Anal Ctr, Ibaraki, Osaka 5670057, Japan
关键词
GALACTOSE-OXIDASE; COPPER; ACTIVATION; CATION;
D O I
10.1021/jacs.5b04104
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of [Cu-I(TIPT(3)tren) (CH3CN)]ClO4 (1) and cumene hydroperoxide (C6H5C-(CH3)(2)OOH, ROOH) at-60 degrees C in CH2Cl2 gave a Cu-II- alkylperoxide/anilino radical complex 2, the formation of which was confirmed by UV vis, resonance Raman, EPR, and CSI-mass spectroscopy. The mechanism of formation of 2, as well as its reactivity, has been explored.
引用
收藏
页码:10870 / 10873
页数:4
相关论文
共 21 条
[1]   Spectroscopic and theoretical studies of mononuclear copper(II) alkyl- and hydroperoxo complexes: Electronic structure contributions to reactivity [J].
Chen, P ;
Fujisawa, K ;
Solomon, EI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) :10177-10193
[2]   Spectroscopic and computational characterization of CuII-OOR (R = H or cumyl) complexes bearing a Me6-tren ligand [J].
Choi, Yu Jin ;
Cho, Kyung-Bin ;
Kubo, Minoru ;
Ogura, Takashi ;
Karlin, Kenneth D. ;
Cho, Jaeheung ;
Nam, Wonwoo .
DALTON TRANSACTIONS, 2011, 40 (10) :2234-2241
[3]   REACTIVE IRON PORPHYRIN DERIVATIVES RELATED TO THE CATALYTIC CYCLES OF CYTOCHROME-P-450 AND PEROXIDASE - STUDIES OF THE MECHANISM OF OXYGEN ACTIVATION [J].
GROVES, JT ;
WATANABE, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (25) :8443-8452
[4]   Mononuclear copper active-oxygen complexes [J].
Itoh, S .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2006, 10 (02) :115-122
[5]  
Kadish K. M., 2000, PORPHYRIN HDB BIOCH, V4
[6]  
Karlin K.D., 2011, Copper-Oxygen Chemistry, V4
[7]   SYNTHESIS, MOLECULAR-STRUCTURE, AND REACTIVITY OF (ALKYLPEROXO)COPPER(II) COMPLEX [J].
KITAJIMA, N ;
KATAYAMA, T ;
FUJISAWA, K ;
IWATA, Y ;
MOROOKA, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (17) :7872-7873
[8]   Aromatic hydroxylation reactivity of a mononuclear Cu(II)-alkylperoxo complex [J].
Kunishita, Atsushi ;
Teraoka, Junji ;
Scanlon, Joseph D. ;
Matsumoto, Takahiro ;
Suzuki, Masatatsu ;
Cramer, Christopher J. ;
Itoh, Shinobu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (23) :7248-+
[9]   Elaboration of copper-oxygen mediated C-H activation chemistry in consideration of future fuel and feedstock generation [J].
Lee, Jung Yoon ;
Karlin, Kenneth D. .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2015, 25 :184-193
[10]   Reactivity of dioxygen-copper systems [J].
Lewis, EA ;
Tolman, WB .
CHEMICAL REVIEWS, 2004, 104 (02) :1047-1076