The key intermediate in the amination of saturated C-H bonds: synthesis, X-ray characterization and catalytic activity of Ru(TPP)(NAr)2 (Ar=3,5-(CF3)2C6H3)

被引:95
作者
Fantauzzi, Simone [1 ,2 ]
Gallo, Emma [1 ,2 ]
Caselli, Alessandro [1 ,2 ]
Ragaini, Fabio [1 ,2 ]
Casati, Nicola [2 ,3 ]
Macchi, Piero [4 ]
Cenini, Sergio [1 ,2 ]
机构
[1] Univ Milan, Dipartimento Chim Inorgan Metallorgan & Analit L, I-20133 Milan, Italy
[2] CNR, ISTM, I-20133 Milan, Italy
[3] Univ Milan, Dipartimento Chim Strutturale & Stereochim Inorga, I-20133 Milan, Italy
[4] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland
关键词
TRANSITION-METAL-COMPLEXES; HYDROGEN-ATOM TRANSFER; RUTHENIUM PORPHYRINS; MANGANESE-PORPHYRINS; ARYL AZIDES; INTRAMOLECULAR AMIDATION; AZIRIDINATION; HYDROCARBONS; FUNCTIONALIZATION; ACTIVATION;
D O I
10.1039/b903238j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The complex Ru(TPP)(NAr)(2) inserts a nitrene group into allylic and benzylic C-H bonds and is the key intermediate in the ruthenium porphyrin-catalyzed amination of hydrocarbons by aryl azides.
引用
收藏
页码:3952 / 3954
页数:3
相关论文
共 30 条
[1]   Amidation of unfunctionalized hydrocarbons catalyzed by ruthenium cyclic amine or bipyridine complexes [J].
Au, SM ;
Huang, JS ;
Che, CM ;
Yu, WY .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7858-7864
[2]   Synthesis, characterisation and reactivity of novel bis(tosyl)imidoruthenium(VI) porphyrin complexes; X-ray crystal structure of a tosylamidoruthenium(IV) porphyrin [J].
Au, SM ;
Fung, WH ;
Cheng, MC ;
Che, CM ;
Peng, SM .
CHEMICAL COMMUNICATIONS, 1997, (17) :1655-1656
[3]   Aziridination of alkenes and amidation of alkanes by bis(tosylimido)ruthenium(VI) porphyrins. A mechanistic study [J].
Au, SM ;
Huang, JS ;
Yu, WY ;
Fung, WH ;
Che, CM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (39) :9120-9132
[4]   Allylic amination and aziridination of olefins by aryl azides catalyzed by Co II(tpp):: A synthetic and mechanistic study [J].
Caselli, Alessandro ;
Gallo, Emma ;
Fantauzzi, Simone ;
Morlacchi, Simona ;
Ragaini, Fabio ;
Cenini, Sergio .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2008, (19) :3009-3019
[5]   Coordination chemistry of organic azides and amination reactions catalyzed by transition metal complexes [J].
Cenini, Sergio ;
Gallo, Emma ;
Caselli, Alessandro ;
Ragaini, Fabio ;
Fantauzzi, Simone ;
Piangiolino, Cristiana .
COORDINATION CHEMISTRY REVIEWS, 2006, 250 (11-12) :1234-1253
[6]   Highly efficient ruthenium(II) porphyrin catalyzed amidation of aldehydes [J].
Chang, Joyce Wei Wei ;
Chan, Philip Wai Hong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (06) :1138-1140
[7]   Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion [J].
Davies, Huw M. L. ;
Manning, James R. .
NATURE, 2008, 451 (7177) :417-424
[8]   Coinage metal catalyzed C-H bond functionalization of hydrocarbons [J].
Diaz-Requejo, M. Mar ;
Perez, Pedro J. .
CHEMICAL REVIEWS, 2008, 108 (08) :3379-3394
[9]   The (porphyrin)ruthenium-catalyzed aziridination of olefins using aryl azides as nitrogen sources [J].
Fantauzzi, Simone ;
Gallo, Emma ;
Caselli, Alessandro ;
Piangiolino, Cristiana ;
Ragaini, Fabio ;
Cenini, Sergio .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (36) :6053-6059
[10]   Nitrene transfer reactions mediated by metallo-porphyrin complexes [J].
Fantauzzi, Simone ;
Caselli, Alessandro ;
Gallo, Emma .
DALTON TRANSACTIONS, 2009, (28) :5434-5443