Coinage metal catalyzed C-H bond functionalization of hydrocarbons

被引:651
作者
Diaz-Requejo, M. Mar [1 ]
Perez, Pedro J. [1 ]
机构
[1] Univ Huelva, Unidad Asociada CSIC, Dept Quim & Ciencia Mat, Lab Catalisis Homogenea, Huelva 21007, Spain
关键词
D O I
10.1021/cr078364y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highlight is given regarding the use of copper-, silver- and gold-based catalysts for the catalytic conversion of unreactive hydrocarbons to a more elaborate and functionalized molecules. An emphasis will given on the reactions where a saturated carbon-hydrogen bond of the hycrocarbon is converted into another functionality. Most often, the overall transformation is composed of the insertion of an X group into the C-H bond followed by a less frequent reaction that assumes the loss of hydrogen in the final product, and finally, the formation of an unsaturated bond which is C=X. The coinage metal-based catalytic systems has an interesting common feature in that it has no M-C and/pr M-H bonds that are formed by any activation process. In addition, a discussion is also given with those catalytic systems that are based on the coinage metals that assumes the functionalization of carbon-hydrogen bonds of nonactivated substrates. The catalytic systems are divided into three types which are: the functionalization by carbene insertion, functionalization by nitrene insertion, and the direct oxidation with a strong oxidant.
引用
收藏
页码:3379 / 3394
页数:16
相关论文
共 113 条
[1]   A simple copper catalyst for both aziridination of alkenes and amination of activated hydrocarbons with chloramine-T trihydrate [J].
Albone, DP ;
Aujla, PS ;
Taylor, PC ;
Challenger, S ;
Derrick, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9569-9571
[2]   Amination of ethers using chloramine-T hydrate and a copper(I) catalyst [J].
Albone, DP ;
Challenger, S ;
Derrick, AM ;
Fillery, SM ;
Irwin, JL ;
Parsons, CM ;
Takada, H ;
Taylor, PC ;
Wilson, DJ .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :107-111
[3]  
[Anonymous], 1990, Selective Hydrocarbon Activation
[4]   Catalysis research of relevance to carbon management: Progress, challenges, and opportunities [J].
Arakawa, H ;
Aresta, M ;
Armor, JN ;
Barteau, MA ;
Beckman, EJ ;
Bell, AT ;
Bercaw, JE ;
Creutz, C ;
Dinjus, E ;
Dixon, DA ;
Domen, K ;
DuBois, DL ;
Eckert, J ;
Fujita, E ;
Gibson, DH ;
Goddard, WA ;
Goodman, DW ;
Keller, J ;
Kubas, GJ ;
Kung, HH ;
Lyons, JE ;
Manzer, LE ;
Marks, TJ ;
Morokuma, K ;
Nicholas, KM ;
Periana, R ;
Que, L ;
Rostrup-Nielson, J ;
Sachtler, WMH ;
Schmidt, LD ;
Sen, A ;
Somorjai, GA ;
Stair, PC ;
Stults, BR ;
Tumas, W .
CHEMICAL REVIEWS, 2001, 101 (04) :953-996
[5]   SELECTIVE INTERMOLECULAR CARBON-HYDROGEN BOND ACTIVATION BY SYNTHETIC METAL-COMPLEXES IN HOMOGENEOUS SOLUTION [J].
ARNDTSEN, BA ;
BERGMAN, RG ;
MOBLEY, TA ;
PETERSON, TH .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) :154-162
[6]   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
[7]  
BARTON DHR, 1991, TETRAHEDRON, V47, P6561
[8]   THE CARBOXYLATION OF SATURATED-HYDROCARBONS BY GIF SYSTEMS (FE(0)/CO/O2 AND CU(0)/CO/O2 IN PYRIDINE-ACETIC ACID) [J].
BARTON, DHR ;
CSUHAI, E ;
DOLLER, D .
TETRAHEDRON LETTERS, 1992, 33 (31) :4389-4392
[9]   THE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .19. APPLICATION OF TERT-BUTYL HYDROPEROXIDE AND DIOXYGEN USING SOLUBLE FE(III) AND CU(II) CHELATES [J].
BARTON, DHR ;
BEVIERE, SD ;
HILL, DR .
TETRAHEDRON, 1994, 50 (09) :2665-2670
[10]   THE SELECTIVE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS - GIF CHEMISTRY [J].
BARTON, DHR ;
DOLLER, D .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (11) :504-512