C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation

被引:2085
作者
Song, Guoyong [1 ]
Wang, Fen [1 ]
Li, Xingwei [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
关键词
INTRAMOLECULAR ALKANE ARYLATION; INTERNAL ALKYNES; BENZOIC-ACIDS; COUPLING REACTIONS; RHODIUM; RH; OLEFINATION; DERIVATIVES; CLEAVAGE; FUNCTIONALIZATION;
D O I
10.1039/c2cs15281a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Rhodium(III)-catalyzed direct functionalization of C-H bonds under oxidative conditions leading to C-C, C-N, and C-O bond formation is reviewed. Various arene substrates bearing nitrogen and oxygen directing groups are covered in their coupling with unsaturated partners such as alkenes and alkynes. The facile construction of C-E (E = C, N, S, or O) bonds makes Rh(III) catalysis an attractive step-economic approach to value-added molecules from readily available starting materials. Comparisons and contrasts between rhodium(III) and palladium(II)-catalyzed oxidative coupling are made. The remarkable diversity of structures accessible is demonstrated with various recent examples, with a proposed mechanism for each transformation being briefly summarized (critical review, 138 references).
引用
收藏
页码:3651 / 3678
页数:28
相关论文
共 137 条
[1]   Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds [J].
Ackermann, Lutz ;
Lygin, Alexander V. ;
Hofmann, Nora .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6379-6382
[2]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[3]   2(1H)-QUINOLINONES WITH CARDIAC STIMULANT ACTIVITY .2. SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF 6-(N-LINKED, 5-MEMBERED HETEROARYL) DERIVATIVES [J].
ALABASTER, CT ;
BELL, AS ;
CAMPBELL, SF ;
ELLIS, P ;
HENDERSON, CG ;
MORRIS, DS ;
ROBERTS, DA ;
RUDDOCK, KS ;
SAMUELS, GMR ;
STEFANIAK, MH .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (03) :575-583
[4]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[5]  
Anastas P., 1998, GREEN CHEM THEORY PR
[6]   (ETA-6-BENZENE)(ETA-5-ETHYLTETRAMETHYLCYCLOPENTADIENYL)RHODIUM (III) HEXAFLUOROPHOSPHATE - A REAGENT FOR CATALYTIC PHENOL OXIDATIVE COUPLING [J].
BARRETT, AGM ;
ITOH, T ;
WALLACE, EM .
TETRAHEDRON LETTERS, 1993, 34 (14) :2233-2234
[7]   Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].
Baudoin, Olivier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911
[8]   C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Sottocornola, Silvia .
CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365
[9]   RhIII-Catalyzed Oxidative Olefination of Vinylic C-H Bonds: Efficient and Selective Access to Di-unsaturated α-Amino Acid Derivatives and Other Linear 1,3-Butadienes [J].
Besset, Tatiana ;
Kuhl, Nadine ;
Patureau, Frederic W. ;
Glorius, Frank .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (26) :7167-7171
[10]   Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].
Boele, MDK ;
van Strijdonck, GPF ;
de Vries, AHM ;
Kamer, PCJ ;
de Vries, JG ;
van Leeuwen, PWNM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587