Facile Benzo-Ring Construction via Palladium-Catalyzed Functionalization of Unactivated sp3 C-H Bonds under Mild Reaction Conditions

被引:137
作者
Feng, Yiqing [1 ]
Wang, Yuji [1 ]
Landgraf, Bradley [1 ]
Liu, Shi [1 ]
Chen, Gong [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词
ORGANOPALLADIUM(IV) CHEMISTRY; ORGANOMETALLIC CHEMISTRY; COUPLING REACTIONS; ORGANIC-MOLECULES; ROOM-TEMPERATURE; DIRECT ARYLATION; DIRECTING GROUP; AMINO-ACIDS; ACTIVATION; MECHANISM;
D O I
10.1021/ol101220x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical synthetic method for the annulation of benzo-rings by the intramolecular coupling of an aryl Iodide and a methylene C H bond is described. The palladium-catalyzed C-H functionalization Is directed by an aminoquinoline carboxamide group, which can be easily installed and removed. High yields and broad substrate scope were achieved. An additive of ortho-phenyl benzoic acid, identified from a systematic screening, functions as a critical ligand for the catalytic process under mild condition, even at near room temperature.
引用
收藏
页码:3414 / 3417
页数:4
相关论文
共 52 条
[1]   A NEW PHOTOCHEMICAL REACTION [J].
BARTON, DHR ;
BEATON, JM ;
GELLER, LE ;
PECHET, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (10) :2640-2641
[2]  
Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
[3]   REMOTE FUNCTIONALIZATION OF STEROIDS BY A RADICAL RELAY MECHANISM [J].
BRESLOW, R ;
CORCORAN, RJ ;
SNIDER, BB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (21) :6791-6792
[4]   DEVELOPMENT OF ORGANOPALLADIUM(IV) CHEMISTRY - FUNDAMENTAL-ASPECTS AND SYSTEMS FOR STUDIES OF MECHANISM IN ORGANOMETALLIC CHEMISTRY AND CATALYSIS [J].
CANTY, AJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (02) :83-90
[5]   A complex catalytic cycle leading to a regioselective synthesis of o,o'-disubstituted vinylarenes [J].
Catellani, M ;
Frignani, F ;
Rangoni, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :119-122
[6]   Synthesis of 3,4-Dihydroisoquinolines by a C(sp3)-H Activation/Electrocyclization Strategy: Total Synthesis of Coralydine [J].
Chaumontet, Manon ;
Piccardi, Riccardo ;
Baudoin, Olivier .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :179-182
[7]   Thermal, catalytic, regiospecific functionalization of alkanes [J].
Chen, HY ;
Schlecht, S ;
Semple, TC ;
Hartwig, JF .
SCIENCE, 2000, 287 (5460) :1995-1997
[8]   1,3-diol synthesis via controlled, radical-mediated C-H functionalization [J].
Chen, Ke ;
Richter, Jeremy M. ;
Baran, Phil S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) :7247-+
[9]   Total synthesis of eudesmane terpenes by site-selective C-H oxidations [J].
Chen, Ke ;
Baran, Phil S. .
NATURE, 2009, 459 (7248) :824-828
[10]   A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis [J].
Chen, Mark S. ;
White, M. Christina .
SCIENCE, 2007, 318 (5851) :783-787