1,1,1-tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols

被引：387

作者：

Chen, Yao-Jung ^{[1
]}

Chen, Hsin-Hung ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 24期

关键词：

D O I：

10.1021/ol062339h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,1,1-Tris(hydroxymethyl)ethane was presented as a new, efficient, and versatile tridentate O-donor ligand suitable for the copper-catalyzed formation of C-N, C-S, and C-O bonds. This inexpensive and commercially available tripod ligand has been demonstrated to facilitate the copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols to afford the corresponding desired products in good to excellent yields.

引用

页码：5609 / 5612

页数：4

共 44 条

[1] Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].

Aranyos, A ;

Old, DW ;

Kiyomori, A ;

Wolfe, JP ;

Sadighi, JP ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378

[2] Palladium-catalyzed reaction of aryl halides with ureas [J].

Artamkina, GA ;

Sergeev, AG ;

Beletskaya, IP .

TETRAHEDRON LETTERS, 2001, 42 (26) :4381-4384

[3] A general method for the formation of aryl-sulfur bonds using copper(I) catalysts [J].

Bates, CG ;

Gujadhur, RK ;

Venkataraman, D .

ORGANIC LETTERS, 2002, 4 (16) :2803-2806

[4] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[5] Ullmann diaryl ether synthesis: Rate acceleration by 2,2,6,6-tetramethylheptane-3,5-dione [J].

Buck, E ;

Song, ZJ ;

Tschaen, D ;

Dormer, PG ;

Volante, RP ;

Reider, PJ .

ORGANIC LETTERS, 2002, 4 (09) :1623-1626

[6] 3-aryl-2-oxazolidinones through the palladium-catalyzed N-arylation of 2-oxazolidinones [J].

Cacchi, S ;

Fabrizi, G ;

Goggiamani, A ;

Zappia, G .

ORGANIC LETTERS, 2001, 3 (16) :2539-2541

[7] Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides [J].

Cristau, HJ ;

Cellier, PP ;

Spindler, JF ;

Taillefer, M .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5607-5622

[8] A general and mild Ullmann-type synthesis of diaryl ethers [J].

Cristau, HJ ;

Cellier, PP ;

Hamada, S ;

Spindler, JF ;

Taillefer, M .

ORGANIC LETTERS, 2004, 6 (06) :913-916

[9] CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands [J].

Deng, W ;

Zou, Y ;

Wang, YF ;

Liu, L ;

Guo, QX .

SYNLETT, 2004, (07) :1254-1258

[10]

Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222

← 1 2 3 4 5 →