Palladium-Catalyzed C-H Perfluoroalkylation of Arenes

被引：109

作者：

Loy, Rebecca N. ^{[1
]}

Sanford, Melanie S. ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 10期

关键词：

VALENT METAL-COMPLEXES; AROMATIC-COMPOUNDS; ASYMMETRIC FLUORINATION; REDUCTIVE ELIMINATION; TRIFLUOROMETHYLATION; FLUOROALKYLATION; ARYLATION; IODIDES; FLUOROCARBONS; ALKYLATION;

D O I：

10.1021/ol200628n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new Pd-catalyzed reaction for the coupling between perfluoroalkyl Iodides (RFI) and simple aromatic substrates is described. The perfluoroalkylated arene products are obtained In good to excellent yields in the presence of a phosphine-ligated Pd catalyst and Cs2CO3 as a base. The development, optimization, scope, and preliminary mechanistic studies of these transformations are reported.

引用

收藏

页码：2548 / 2551

页数：4

相关论文

共 54 条

[1] Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV) [J].

Ball, Nicholas D. ;

Kampf, Jeff W. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) :2878-+

[2] Palladium-catalyzed phenyl-selenylation with n-Bu3SnSePh in one-pot two-step reactions [J].

Bonaterra, Mariana ;

Martin, Sandra E. ;

Rossi, Roberto A. .

TETRAHEDRON LETTERS, 2006, 47 (21) :3511-3515

[3] (Diacetoxyiodo)benzene-lithium bromide as a convenient electrophilic Br+ source [J].

Braddock, DC ;

Cansell, G ;

Hermitage, SA .

SYNLETT, 2004, (03) :461-464

[4] New methods of free-radical perfluoroalkylation of aromatics and alkenes. Absolute rate constants and partial rate factors for the homolytic aromatic substitution by n-perfluorobutyl radical [J].

Bravo, A ;

Bjorsvik, HR ;

Fontana, F ;

Liguori, L ;

Mele, A ;

Minisci, F .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7128-7136

[5] 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

[6] PREPARATION OF DIALKYL CARBONATES VIA THE PHASE-TRANSFER-CATALYZED ALKYLATION OF ALKALI-METAL CARBONATE AND BICARBONATE SALTS [J].

CELLA, JA ;

BACON, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (06) :1122-1125

[7] STUDIES ON FLUOROALKYLATION AND FLUOROALKOXYLATION .28. PALLADIUM(O)-INDUCED ADDITION OF FLUOROALKYL IODIDES TO ALKENES - AN ELECTRON-TRANSFER PROCESS [J].

CHEN, QY ;

YANG, ZY ;

ZHAO, CX ;

QIU, ZM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03) :563-567

[8] Two methods for direct ortho-arylation of benzoic acids [J].

Chiong, Hendrich A. ;

Pham, Quynh-Nhu ;

Daugulis, Olafs .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (32) :9879-9884

[9] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].

Cho, Eun Jin ;

Senecal, Todd D. ;

Kinzel, Tom ;

Zhang, Yong ;

Watson, Donald A. ;

Buchwald, Stephen L. .

SCIENCE, 2010, 328 (5986) :1679-1681

[10] Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids [J].

Chu, Lingling ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2010, 12 (21) :5060-5063

← 1 2 3 4 5 6 →