A facile, microwave-assisted, palladium-catalyzed arylation of acetone

被引：19

作者：

Chobanian, Harry R. ^{[1
]}

Liu, Ping ^{[1
]}

Chioda, Marc D. ^{[1
]}

Guo, Yan ^{[1
]}

Lin, Linus S. ^{[1
]}

机构：

[1] Merck & Co Inc, Merck Res Labs, Dept Med Chem, Rahway, NJ 07065 USA

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 07期

关键词：

D O I：

10.1016/j.tetlet.2006.12.060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an expedient method for the heteroarylation of acetone tinder tin-free conditions. The coupling is performed using the commercially available enol silane of acetone (2-trimethylsilyloxypropene) and a corresponding ary, bromide, chloride or triflate under microwave-assisted conditions, with tris(dibenzylideneacetonc)dipalladium (Pd-2(dba)(3)) or palladium acetate (Pd(OAc)(2)) and 2-(2',6'-dimethoxybiphenyl)dicyclohexylphosphine (S-Phos) as the catalyst system. Published by Elsevier Ltd.

引用

页码：1213 / 1216

页数：4

共 9 条

[1] POTASSIUM FLUORIDE ON CELITE - VERSATILE REAGENT FOR C-ALKYLATION,N-ALKYLATION,O-ALKYLATION, AND S-ALKYLATION [J].

ANDO, T ;

YAMAWAKI, J .

CHEMISTRY LETTERS, 1979, (01) :45-46

[2] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[3] A facile microwave-assisted palladium-catalyzed cyanation of aryl chlorides [J].

Chobanian, HR ;

Fors, BP ;

Lin, LS .

TETRAHEDRON LETTERS, 2006, 47 (19) :3303-3305

[4] Palladium-catalyzed regiocontrolled α-arylation of trimethylsilyl enol ethers with aryl halides [J].

Iwama, Tetsuo ;

Rawal, Viresh H. .

ORGANIC LETTERS, 2006, 8 (25) :5725-5728

[5] Controlled microwave heating in modern organic synthesis [J].

Kappe, CO .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6250-6284

[6] REGIOSELECTIVE ARYLATION OF SILYL ENOL ETHERS OF METHYL KETONES WITH ARYL BROMIDES [J].

KUWAJIMA, I ;

URABE, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (24) :6831-6833

[7]

LEWIS CN, 1986, SYNTHESIS-STUTTGART, P944

[8] A highly active catalyst system for the heteroarylation of acetone [J].

Liu, P ;

Lanza, TJ ;

Jewell, JP ;

Jones, CP ;

Hagmann, WK ;

Lin, LS .

TETRAHEDRON LETTERS, 2003, 44 (49) :8869-8871

[9] Mild palladium-catalyzed selective monoarylation of nitriles [J].

Wu, LY ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) :15824-15832

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