Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage

被引:318
作者
Fukutani, Tatsuya [1 ]
Umeda, Nobuyoshi [1 ]
Hirano, Koji [1 ]
Satoh, Tetsuya [1 ]
Miura, Masahiro [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
关键词
BENZOIC-ACIDS; DIRECT ARYLATION; ACTIVATION; FUNCTIONALIZATION; PYRIDINES; RH; IMINOANNULATION; ISOQUINOLINES; ALKENYLATION; PHENYLAZOLES;
D O I
10.1039/b910198e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The rhodium-catalyzed oxidative coupling of aromatic imines with alkynes effectively proceeds via regioselective C-H bond cleavage to produce indenone imine and isoquinoline derivatives.
引用
收藏
页码:5141 / 5143
页数:3
相关论文
共 55 条
[1]  
Ackermann L, 2007, TOP ORGANOMETAL CHEM, V24, P35, DOI 10.1007/3418_2007_062
[2]   Synthesis and structure-activity relationship of novel indene N-oxide derivatives as potent peroxisome proliferator activated receptor γ (PPARγ) agonists [J].
Ahn, Jin Hee ;
Shin, Mi Sik ;
Jung, Sun Ho ;
Kim, Jin Ah ;
Kim, Hye Min ;
Kim, Se Hoan ;
Kanga, Seung Kyu ;
Kim, Kwang Rok ;
Dal Rhee, Sang ;
Park, Sung Dae ;
Lee, Jae Mok ;
Lee, Jeong Hyung ;
Cheon, Hyae Gyeong ;
Kim, Sung Soo .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (18) :5239-5244
[3]   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
[4]   Direct, two-step synthetic pathway to novel dibenzo[a,c]phenanthridines [J].
Churruca, F ;
SanMartin, R ;
Carril, M ;
Urtiaga, MK ;
Solans, X ;
Tellitu, I ;
Domínguez, E .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3178-3187
[5]   Synthesis of dihydropyridines and pyridines from Imines and alkynes via C-H activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3645-3651
[6]   Design and study of homogeneous catalysts for the selective, low temperature oxidation of hydrocarbons [J].
Conley, Brian L. ;
Tenn, William J., III ;
Young, Kenneth J. H. ;
Ganesh, Somesh K. ;
Meier, Steven K. ;
Ziatdinov, Vadim R. ;
Mironov, Oleg ;
Oxgaard, Jonas ;
Gonzales, Jason ;
Goddard, William A., III ;
Periana, Roy A. .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 251 (1-2) :8-23
[7]  
Durr U, 1997, SYNLETT, P1335
[8]  
Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO
[9]  
2-6
[10]   C-H bond functionalizations with palladium(II): intramolecular oxidative annulations of arenes [J].
Ferreira, Eric M. ;
Zhang, Haiming ;
Stoltz, Brian M. .
TETRAHEDRON, 2008, 64 (26) :5987-6001