Renaissance of Ullmann and Goldberg reactions - Progress in copper catalyzed C-N-, C-O- and C-S-coupling

被引:805
作者
Kunz, K [1 ]
Scholz, U
Ganzer, D
机构
[1] Bayer CropSci AG Res, Chem Fungicides, D-51368 Leverkusen, Germany
[2] Bayer Chem AG, Fine Chem Res & Dev, D-51368 Leverkusen, Germany
关键词
catalysis; cross-coupling; copper; arylations; nucleophilic aromatic substitution;
D O I
10.1055/s-2003-42473
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-catalyzed C-N-, C-O- and C-S-coupling reactions are powerful tools in organic synthesis and have been extensively reinvestigated in the past five years. The understanding of solubilizing and accelerating effects exhibited by substrates and ligands initiated novel developments originally on N-arylation of amines, amides, and nitrogen heterocycles. Nevertheless practical methods for the syntheses of aryl ethers and aryl thioethers have been established as well. A wide range of arylating reagents was explored, of which the aryl halides will be presented in this overview. Among a growing set of ligands and optimized reaction protocols, the most promising procedures are highlighted, covering the literature published through May 2003.
引用
收藏
页码:2428 / 2439
页数:12
相关论文
共 69 条
[31]  
Kang SK, 2002, SYNLETT, P427
[32]   Copper-catalyzed amination of aryl halides: single-step synthesis of triarylamines [J].
Kelkar, AA ;
Patil, NM ;
Chaudhari, RV .
TETRAHEDRON LETTERS, 2002, 43 (40) :7143-7146
[33]   An efficient copper-catalyzed coupling of aryl halides with imidazoles [J].
Kiyomori, A ;
Marcoux, JF ;
Buchwald, SL .
TETRAHEDRON LETTERS, 1999, 40 (14) :2657-2660
[34]   A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles [J].
Klapars, A ;
Antilla, JC ;
Huang, XH ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7727-7729
[35]   A general and efficient copper catalyst for the amidation of aryl halides [J].
Klapars, A ;
Huang, XH ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) :7421-7428
[36]   Mild and efficient copper-catalyzed amination of aryl bromides with primary alkylamines [J].
Kwong, FY ;
Buchwald, SL .
ORGANIC LETTERS, 2003, 5 (06) :793-796
[37]   A general, efficient, and inexpensive catalyst system for the coupling of aryl iodides and thiols [J].
Kwong, FY ;
Buchwald, SL .
ORGANIC LETTERS, 2002, 4 (20) :3517-3520
[38]   Copper-catalyzed coupling of alkylamines and aryl iodides: An efficient system even in an air atmosphere [J].
Kwong, FY ;
Klapars, A ;
Buchwald, SL .
ORGANIC LETTERS, 2002, 4 (04) :581-584
[39]   New aryl/heteroaryl C-N bond cross-coupling reactions via arylboronic acid cupric acetate arylation [J].
Lam, PYS ;
Clark, CG ;
Saubern, S ;
Adams, J ;
Winters, MP ;
Chan, DMT ;
Combs, A .
TETRAHEDRON LETTERS, 1998, 39 (19) :2941-2944
[40]   Amination of aryl halides using copper catalysis [J].
Lang, FR ;
Zewge, D ;
Houpis, IN ;
Volante, RP .
TETRAHEDRON LETTERS, 2001, 42 (19) :3251-3254