Reactions of nitroxides with metalloporphyrin alkyls bearing beta hydrogens: Aliphatic carbon-carbon bond activation by metal centered radicals

被引:21
作者
Chan, Kin Shing [1 ]
Mak, Kin Wah [1 ]
Tse, Man Kin [1 ]
Yeung, Siu Kwan [1 ]
Li, Bao Zhu [1 ]
Chan, Yun Wai [1 ]
机构
[1] Chinese Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
关键词
rhodium porphyrin; nitroxides; carbon-carbon bond activation;
D O I
10.1016/j.jorganchem.2007.11.009
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Nitroxide-induced beta-hydrogen atom abstraction and beta-elimination of rhodium porphyrin alkyls have been observed. Rhodium(II) porphyrin radical were proposed intermediates to form first and subsequently reacted via aliphatic carbon-carbon bond activation with alkyl substituted nitroxides to yield rhodium porphyrin alkyl complexes. (C) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:399 / 407
页数:9
相关论文
共 43 条
[1]   A warning on the use of radical traps as a test for radical mechanisms:: They react with palladium hydrido complexes [J].
Albéniz, AC ;
Espinet, P ;
López-Fernández, R ;
Sen, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11278-11279
[2]  
Alder A. D., 1967, J ORG CHEM, V32, P476
[3]   Symmetrical nitroxide synthesis:: Meso versus d,l diastereomer formation [J].
Braslau, R ;
Chaplinski, V ;
Goodson, P .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9857-9864
[4]   SYNTHESES OF RHODIUM AND IRIDIUM (OCTAETHYLPORPHYRINATO)METAL DIMERS FROM TEMPO [J].
CHAN, KS ;
LEUNG, YB .
INORGANIC CHEMISTRY, 1994, 33 (14) :3187-3187
[5]  
Chorghade MS, 1996, SYNTHESIS-STUTTGART, P1320
[6]   SIGMA-ASSISTED EXCHANGE INTERACTIONS IN LINEAR ADDUCTS OF NITROXIDES WITH DIRHODIUM TETRAKIS(TRIFLUOROACETATE) [J].
COGNE, A ;
GRAND, A ;
REY, P ;
SUBRA, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7927-7929
[7]   RADICAL MECHANISM FOR THE DECOMPOSITION OF RUOEP(CH2CH3)2 - DETERMINATION OF THE METAL-CARBON BOND-DISSOCIATION ENERGY [J].
COLLMAN, JP ;
MCELWEEWHITE, L ;
BROTHERS, PJ ;
ROSE, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (06) :1332-1333
[8]   Efficient and selective aerobic oxidation of alcohols into aldehydes and ketones using ruthenium/TEMPO as the catalytic system [J].
Dijksman, A ;
Marino-González, A ;
Payeras, AMI ;
Arends, IWCE ;
Sheldon, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6826-6833
[9]   Polyhaloporphyrins: Unusual ligands for metals and metal-catalyzed oxidations [J].
Dolphin, D ;
Traylor, TG ;
Xie, LY .
ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (06) :251-259
[10]   MAGNETIC EXCHANGE INTERACTIONS IN NITROXYL BIRADICALS BRIDGED BY METAL METAL BONDED COMPLEXES - STRUCTURAL, MAGNETOCHEMICAL, AND ELECTRONIC SPECTRAL CHARACTERIZATION OF TETRAKIS(PERFLUOROCARBOXYLATO)DIMETAL(II) COMPLEXES OF RHODIUM AND MOLYBDENUM CONTAINING AXIALLY COORDINATED NITROXYL RADICALS [J].
FELTHOUSE, TR ;
DONG, TY ;
HENDRICKSON, DN ;
SHIEH, HS ;
THOMPSON, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (26) :8201-8214