Palladium-Catalyzed Oxidative Insertion of Carbon Monoxide to N-Sulfonyl-2-aminobiaryls through C-H Bond Activation: Access to Bioactive Phenanthridinone Derivatives in One Pot

被引:123
作者
Rajeshkumar, Venkatachalam [1 ]
Lee, Tai-Hua [1 ]
Chuang, Shih-Ching [1 ]
机构
[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 30010, Taiwan
关键词
REGIOSELECTIVE SYNTHESIS; CARBONYLATION REACTIONS; CHEMICAL-CONSTITUENTS; C(SP(3))-H BONDS; ARYL HALIDES; ALKALOIDS; CYCLIZATION; C(SP(2))-H; HIPPADINE; ALKENES;
D O I
10.1021/ol4001922
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed oxidative carbonylation of N-sulfonyl-2-aminobiaryls through C-H bond activation and C-C, C-N bond formation under TFA-free and milder conditions has been developed. The reaction tolerates a variety of substrates and provides biologically important phenanthrldlnone derivatives in yields up to 94%.
引用
收藏
页码:1468 / 1471
页数:4
相关论文
共 64 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[3]   Docking studies on PARP-1 inhibitors: insights into the role of a binding pocket water molecule [J].
Bellocchi, D ;
Macchiarulo, A ;
Costantino, G ;
Pellicciari, R .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (04) :1151-1157
[4]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[5]   Synthesis of fluoren-9-ones via palladium-catalyzed cyclocarbonylation of o-halobiaryls [J].
Campo, MA ;
Larock, RC .
ORGANIC LETTERS, 2000, 2 (23) :3675-3677
[6]   Palladium-Catalyzed Double Carbonylation Reactions of o-Dihaloarenes with Amines in Phosphonium Salt Ionic Liquids [J].
Cao, Hong ;
Alper, Howard .
ORGANIC LETTERS, 2010, 12 (18) :4126-4129
[7]   Organic photovoltaics incorporating fulleroisoquinolinones as n-type materials [J].
Chen, Chih-Ping ;
Luo, Charlene ;
Ting, Ching ;
Chuang, Shih-Ching .
CHEMICAL COMMUNICATIONS, 2011, 47 (06) :1845-1847
[8]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[9]   Intramolecular Oxidative C-N Bond Formation for the Synthesis of Carbazoles: Comparison of Reactivity between the Copper-Catalyzed and Metal-Free Conditions [J].
Cho, Seung Hwan ;
Yoon, Jungho ;
Chang, Sukbok .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5996-6005
[10]   Annulation of Benzamides with [60]Fullerene through Palladium(II)-Catalyzed C-H Bond Activation [J].
Chuang, Shih-Ching ;
Rajeshkumar, Venkatachalam ;
Cheng, Chun-An ;
Deng, Jie-Cheng ;
Wang, Guan-Wu .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (06) :1599-1604