Synthesis of Dibenzofurans via Palladium-Catalyzed Phenol-Directed C-H Activation/C-O Cyclization

被引：304

作者：

Xiao, Bin ^{[1
]}

Gong, Tian-Jun ^{[1
]}

Liu, Zhao-Jing ^{[1
]}

Liu, Jing-Hui ^{[1
]}

Luo, Dong-Fen ^{[1
]}

Xu, Jun ^{[1
]}

Liu, Lei ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 24期

关键词：

N BOND FORMATION; ARYL HALIDES; DIRECT ARYLATION; DIARYL ETHERS; AMINATION REACTION; COUPLING REACTIONS; ROUTE; ACIDS; FUNCTIONALIZATION; 2-PHENYLPHENOLS;

D O I：

10.1021/ja203335u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A practical, Pd(0)/Pd(II)-catalyzed reaction was developed for phenol-directed C-H activation/C-O cyclization using air as an oxidant. The turnover-limiting step of the process was found to be C-O reductive elimination instead of C-H activation. This reaction can tolerate a variety of functional groups and is complementary to the previous methods for the synthesis of substituted dibenzofurans.

引用

页码：9250 / 9253

页数：4

共 50 条

[1] Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Althammer, Andreas .

ORGANIC LETTERS, 2008, 10 (11) :2299-2302

[2] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[3]

AMES DE, 1983, SYNTHESIS-STUTTGART, P234

[4] 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

[5] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].

Brasche, Gordon ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934

[6] Allylic C-H Acetoxylation with a 4,5-Diazafluorenone-Ligated Palladium Catalyst: A Ligand-Based Strategy To Achieve Aerobic Catalytic Turnover [J].

Campbell, Alison N. ;

White, Paul B. ;

Guzei, Ilia A. ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) :15116-15119

[7] Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].

Campeau, LC ;

Parisien, M ;

Jean, A ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590

[8] Achyrofuran, a new antihyperglycemic dibenzofuran from the South American medicinal plant Achyrocline satureioides [J].

Carney, JR ;

Krenisky, JM ;

Williamson, RT ;

Luo, J .

JOURNAL OF NATURAL PRODUCTS, 2002, 65 (02) :203-205

[9] A Highly Para-Selective Copper(II)-Catalyzed Direct Arylation of Aniline and Phenol Derivatives [J].

Ciana, Claire-Lise ;

Phipps, Robert J. ;

Brandt, Jochen R. ;

Meyer, Falco-Magnus ;

Gaunt, Matthew J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) :458-462

[10] Selective functionalization of amino acids in water: A synthetic method via catalytic C-H bond activation [J].

Dangel, BD ;

Johnson, JA ;

Sames, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (33) :8149-8150

← 1 2 3 4 5 →