Cu-Catalyzed Arylation of Phenols: Synthesis of Sterically Hindered and Heteroaryl Diaryl Ethers

被引:175
作者
Maiti, Debabrata [1 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
CROSS-COUPLING REACTIONS; ARYL IODIDES; NUCLEOPHILIC-SUBSTITUTION; CUPRIC ACETATE; BOND FORMATION; O BOND; COPPER; HALIDES; LIGAND; EFFICIENT;
D O I
10.1021/jo9026935
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cu-catalyzed O-arylation of phenols with aryl iodides and bromides can be performed under mild condition in DMSO/K3PO4 with use of picolinic acid as the ligand for copper. This method tolerates a variety of functional groups and is effective in the synthesis of hindered diaryl ethers and heteroaryl ethers.
引用
收藏
页码:1791 / 1794
页数:4
相关论文
共 54 条
[1]   Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines [J].
Altman, Ryan A. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2007, 9 (04) :643-646
[2]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[3]   Three groups good, four groups bad?: Atropisomerism in ortho-substituted diaryl ethers [J].
Betson, Mark S. ;
Clayden, Jonathan ;
Worrall, Christopher R. ;
Peace, Simon .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (35) :5803-5807
[4]   Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects [J].
Burgos, Carlos H. ;
Barder, Timothy E. ;
Huang, Xiaohua ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4321-4326
[5]   Mild Ullmann-type biaryl ether formation reaction by combination of ortho-substituent and ligand effects [J].
Cai, Q ;
Zou, BL ;
Ma, DW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) :1276-1279
[6]   Mild and nonracemizing conditions for Ullmann-type diaryl ether formation between aryl iodides and tyrosine derivatives [J].
Cai, Qian ;
He, Gang ;
Ma, Dawei .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5268-5273
[7]   Preparation of a Corticotropin-Releasing Factor Antagonist by Nucleophilic Aromatic Substitution and Copper-Mediated Ether Formation [J].
Caron, Stephane ;
Do, Nga M. ;
Sieser, Janice E. ;
Whritenour, David C. ;
Hill, Paul D. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (02) :324-330
[8]   New N- and O-arylations with phenylboronic acids and cupric acetate [J].
Chan, DMT ;
Monaco, KL ;
Wang, RP ;
Winters, MP .
TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936
[9]   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 [J].
Chen, Yao-Jung ;
Chen, Hsin-Hung .
ORGANIC LETTERS, 2006, 8 (24) :5609-5612
[10]   Efficient nucleophilic substitution reactions of pyrimidyl and pyrazyl halides with nucleophiles, under focused microwave irradiation [J].
Cherng, YH .
TETRAHEDRON, 2002, 58 (05) :887-890