Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation

被引:3369
作者
Colby, Denise A.
Bergman, Robert G. [1 ]
Ellman, Jonathan A.
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
N-HETEROCYCLIC CARBENES; CHELATION-ASSISTED HYDROACYLATION; DIRECT ORTHO ARYLATION; ONE-POT SYNTHESIS; TRANSITION-METAL; CARBON-HYDROGEN; COUPLING REACTION; ORTHO-ALKYLATION; AROMATIC IMINES; INTERMOLECULAR HYDROACYLATION;
D O I
10.1021/cr900005n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several researchers conducted studies to demonstrate rhodium-catalyzed C-C bond formation through heteroatom-directed C-H bond activation. A key issue in the development of C-H bond functionalization method involved the selective reactivity of a targeted C-H bond over the others present in a molecule. Lim and Kang were two researchers who conducted significant studies in the field, employing pyridine groups to direct functionalization. The immune functionality was also widely used and developed in the area of C-H bond functionlization by rhodium (Rh). The Rh-catalyzed alkylation of N-benzyl aryl ketimines was found to have significant scope than the Rh-catalyzed alkylation of aryl ketones in such reactions. The ketimines reacted cleanly with a wider range of alkenes than that was potentially employed in the Rh-mediated aryl ketone alkylation.
引用
收藏
页码:624 / 655
页数:32
相关论文
共 230 条
[1]   [RuCl3(H2O)n]-catalyzed direct arylations [J].
Ackermann, Lutz ;
Althammer, Andreas ;
Born, Robert .
TETRAHEDRON, 2008, 64 (26) :6115-6124
[2]  
Ackermann L, 2007, TOP ORGANOMETAL CHEM, V24, P35, DOI 10.1007/3418_2007_062
[3]   Synthesis of a tricyclic mescaline analogue by catalytic C-H bond activation [J].
Ahrendt, KA ;
Bergman, RG ;
Ellman, JA .
ORGANIC LETTERS, 2003, 5 (08) :1301-1303
[4]   A rhodium-catalyzed C-H activation/cycloisomerization tandem [J].
Aissa, Christophe ;
Fuerstner, Alois .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (48) :14836-+
[5]   Synthesis of tricyclic heterocycles via a tandem aryl alkylation/heck coupling sequence [J].
Alberico, Dino ;
Rudolph, Alena ;
Lautens, Mark .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03) :775-781
[6]   Palladium-catalyzed alkylation-alkenylation reactions: Rapid access to tricyclic mescaline analogues [J].
Alberico, Dino ;
Lautens, Mark .
SYNLETT, 2006, (18) :2969-2972
[7]   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
[8]   Metal-mediated reductive hydrodehalogenation of organic halides [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2002, 102 (11) :4009-4091
[9]   Iridium(III)-induced isomerization of 2-substituted pyridines to N-heterocyclic carbenes [J].
Alvarez, Eleuterio ;
Conejero, Salvador ;
Paneque, Margarita ;
Petronilho, Ana ;
Poveda, Manuel L. ;
Serrano, Oracio ;
Carmona, Ernesto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13060-13061
[10]   Formation and stability of N-heterocyclic carbenes in water:: The carbon acid pKa of imidazollum cations in aqueous solution [J].
Amyes, TL ;
Diver, ST ;
Richard, JP ;
Rivas, FM ;
Toth, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4366-4374