Copper-catalyzed arylation of heterocycle C-H bonds

被引:462
作者
Do, Hien-Quang [1 ]
Daugulis, Olafs [1 ]
机构
[1] Univ Houston, Dept Chem, Houston, TX 77204 USA
关键词
D O I
10.1021/ja075802+
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method for the direct, copper-catalyzed arylation of heterocycle C-H bonds by aryl halides has been developed. In addition to electron-rich five-membered heterocycles, electron-poor pyridine oxides can also be arylated. The best results are obtained by using a combination of lithium tert -butoxide base, aryl iodide coupling partner, and copper iodide catalyst.
引用
收藏
页码:12404 / +
页数:3
相关论文
共 33 条
[1]  
AKITA Y, 1985, HETEROCYCLES, V23, P2327
[2]   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
[3]   Copper-mediated cross-coupling of organostannanes with organic iodides at or below room temperature [J].
Allred, GD ;
Liebeskind, LS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) :2748-2749
[4]   Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions [J].
Bellina, F ;
Cauteruccio, S ;
Rossi, R .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (06) :1379-1382
[5]   Regioselective synthesis of 1,5-diaryl-1H-imidazoles by palladium-catalyzed direct arylation of 1-aryl-1H-imidazoles [J].
Bellina, F ;
Cauteruccio, S ;
Mannina, L ;
Rossi, R ;
Viel, S .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :3997-4005
[6]   Concise synthesis of (±)-rhazinilam through direct coupling [J].
Bowie, AL ;
Hughes, CC ;
Trauner, D .
ORGANIC LETTERS, 2005, 7 (23) :5207-5209
[7]   A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].
Campeau, LC ;
Rousseaux, S ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021
[8]   Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].
Chen, Xiao ;
Hao, Xue-Shi ;
Goodhue, Charles E. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791
[9]   Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides [J].
Chiong, Hendrich A. ;
Daugulis, Olafs .
ORGANIC LETTERS, 2007, 9 (08) :1449-1451
[10]   Biotransformation reactions of five-membered aromatic heterocyclic rings [J].
Dalvie, DK ;
Kalgutkar, AS ;
Khojasteh-Bakht, SC ;
Obach, RS ;
O'Donnell, JP .
CHEMICAL RESEARCH IN TOXICOLOGY, 2002, 15 (03) :269-299