Palladium-catalyzed desulfitative cross-coupling of arylsulfinates with arylboronic acids

被引：27

作者：

Cheng, Kai ^{[1
]}

Yu, Hai-Zhu ^{[2
]}

Zhao, Baoli ^{[1
]}

Hu, Sai ^{[3
]}

Zhang, Xian-Man ^{[1
]}

Qi, Chenze ^{[1
]}

机构：

[1] Shaoxing Univ, Zhejiang Key Lab Alternat Technol Fine Chem Proc, Shaoxing 312000, Peoples R China

[2] Univ Sci & Technol Beijing, Dept Polymer Sci & Engn, Beijing 100083, Peoples R China

[3] Ningbo Univ, Coll Mat Sci & Chem Engn, Ningbo 310014, Zhejiang, Peoples R China

来源：

RSC ADVANCES | 2014年 / 4卷 / 101期

基金：

中国国家自然科学基金;

关键词：

SUZUKI-MIYAURA REACTION; ARYL SULFINIC ACIDS; DIRECT ESI-MS; ARENESULFONYL CHLORIDES; BOND FORMATION; DECARBOXYLATIVE PALLADATION; ARYLSULFONYL CHLORIDES; SULFONYL CHLORIDES; ALKENYL PHOSPHATES; CARBOXYLIC-ACIDS;

D O I：

10.1039/c4ra07455f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Palladium (Pd)-catalyzed desulfitative cross-coupling reactions of sodium arylsulfinates with a wide variety of arylboronic acids were achieved in good to excellent yields under simple aerobic conditions. These catalytic reactions could be accelerated by addition of a catalytic amount of Cu(II) salts as co-catalyst. Moreover, these reactions were tolerant to all of the tested functional groups, making them attractive alternatives to the traditional cross-coupling reactions.

引用

页码：57923 / 57928

页数：6

共 113 条

[31] The Development of Versatile Methods for Palladium-Catalyzed Coupling Reactions of Aryl Electrophiles through the Use of P(t-Bu)3 and PCy3 as Ligands [J].

Fu, Gregory C. .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1555-1564

[32] COUPLING, CARBONYLATION, AND VINYLATION REACTIONS OF AROMATIC SULFINIC ACIDS VIA ORGANOPALLADIUM INTERMEDIATES [J].

GARVES, K .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (10) :3273-&

[33] New synthesis of biaryls via Rh-catalyzed decarbonylative Suzuki-coupling of carboxylic anhydrides with arylboroxines [J].

Goossen, LJ ;

Paetzold, J .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1665-1668

[34] Sterically hindered chelating alkyl phosphines provide large rate accelerations in palladium-catalyzed amination of aryl iodides, bromides, and chlorides, and the first amination of aryl tosylates [J].

Hamann, BC ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) :7369-7370

[35] Investigations on the Suzuki-Miyaura and Negishi couplings with alkenyl phosphates: Application to the synthesis of 1,1-disubstituted alkenes [J].

Hansen, Anders L. ;

Ebran, Jean-Philippe ;

Gogsig, Thomas M. ;

Skrydstrup, Troels .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (17) :6464-6472

[36] Direct synthesis of 1,1-diarylalkenes from alkenyl phosphates via nickel(0)-catalysed Suzuki-Miyaura coupling [J].

Hansen, Anders L. ;

Ebran, Jean-Philippe ;

Gogsig, Thomas M. ;

Skrydstrup, Troels .

CHEMICAL COMMUNICATIONS, 2006, (39) :4137-4139

[37] Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides [J].

Hartwig, John F. .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1534-1544

[38] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].

Hassan, J ;

Sévignon, M ;

Gozzi, C ;

Schulz, E ;

Lemaire, M .

CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469

[39] Pd(O2CCF3)2/Benzoquinone: A Versatile Catalyst System for the Decarboxylative Olefination of Arene Carboxylic Acids [J].

Hu, Peng ;

Kan, Jian ;

Su, Weiping ;

Hong, Maochun .

ORGANIC LETTERS, 2009, 11 (11) :2341-2344

[40] Cross-coupling of organoboronic acids and sulfinate salts using catalytic copper(II) acetate and 1,10-phenanthroline: synthesis of aryl and alkenylsulfones [J].

Huang, Fang ;

Batey, Robert A. .

TETRAHEDRON, 2007, 63 (32) :7667-7672

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