Efficient Copper-Catalyzed Coupling of 2-Haloacetanilides with Phosphine Oxides and Phosphites under Mild Conditions

被引：24

作者：

Jiang, Deshou ^{[1
]}

Jiang, Qun ^{[2
]}

Fu, Hua ^{[1
]}

Jiang, Yuyang ^{[1
,2
]}

Zhao, Yufen ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China

[2] Tsinghua Univ, Grad Sch Shenzhen, Key Lab Chem Biol Guangdong Prov, Shenzhen 518057, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2008年 / 21期

基金：

中国国家自然科学基金;

关键词：

Ullmann reaction; P-arylation; ortho effect; copper catalysis; N; N-ligand;

D O I：

10.1055/s-0028-1083155

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a highly efficient method for the copper-catalyzed coupling of 2-haloacetanilides with phosphine oxides and phosphites in the presence of a catalytic amount of copper(I) iodide and N-methylpyrrolidine-2-carboxamide tinder mild conditions (45-55 degrees C); the P-arylation products were synthesized in good to excellent yields in short times using 2-bromotrifluoroacetanilides and 2-iodotrifluoroacetanilides as the starting materials. This represents the lowest reaction temperatures for copper-catalyzed P-arylation thus far.

引用

页码：3473 / 3477

页数：5

共 28 条

[21] Copper-mediated cross-coupling of H-phosphonates with vinyliodonium salts:: A novel very mild synthesis of 2-arylvinylphosphonates
Thielges, S
Bisseret, P
Eustache, J
[J]. ORGANIC LETTERS, 2005, 7 (04) : 681 - 684
[22] Copper-catalyzed synthesis of unsymmetrical triarylphosphines
Van Allen, D
Venkataraman, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) : 4590 - 4593
[23] DERIVATIVES OF UNSATURATED PHOSPHONIC ACIDS
WELCH, CM
GONZALES, EJ
GUTHRIE, JD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (09) : 3270 - &
[24] CuI/L-proline-catalyzed coupling reactions of aryl halides with activated methylene compounds
Xie, XA
Cai, GR
Ma, DW
[J]. ORGANIC LETTERS, 2005, 7 (21) : 4693 - 4695
[25] Enantioselective arylation of 2-methylacetoacetates catalyzed by CuI/trans-4-hydroxy-L-proline at low reaction temperatures
Xie, Xiaoan
Chen, Yu
Ma, Dawei
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) : 16050 - 16051
[26] Efficient copper-catalyzed amination of aryl halides with amines and N-H heterocycles using rac-BINOL as ligand
Zhu, Di
Wang, Rongliang
Mao, Jincheng
Xu, Lei
Wu, Fan
Wan, Boshun
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 256 (1-2) : 256 - 260
[27] Synthesis of aryl sulfones via L-proline-promoted CuI-catalyzed coupling reaction of aryl halides with sulfinic acid salts
Zhu, W
Ma, DW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) : 2696 - 2700
[28] Synthesis of 1,2-disubstituted benzimidazoles by a Cu-catalyzed cascade aryl amination/condensation process
Zou, Benli
Yuan, Qiliang
Ma, Dawei
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (15) : 2598 - 2601

← 1 2 3 →