An efficient and mild CuI/L-proline-catalyzed arylation of acetylacetone or ethyl cyanoacetate

被引：78

作者：

Jiang, YW ^{[1
]}

Wu, N ^{[1
]}

Wu, HH ^{[1
]}

He, MY ^{[1
]}

机构：

[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

SYNLETT | 2005年 / 18期

关键词：

cross coupling; arylation; aryl iodide; catalysis; additive;

D O I：

10.1055/s-2005-918921

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The coupling reaction of aryl iodides with acetylacetone or ethyl cyanoacetate under catalysis of CuI/L-proline works at relatively mild conditions to provide 3-aryl-2, 4-pentanediones and alpha-aryl cyanoacetates in moderate to good yields.

引用

页码：2731 / 2734

页数：4

共 45 条

[1]

Abele S, 2000, EUR J ORG CHEM, V2000, P1

[2] Copper-catalyzed coupling of arylboronic acids and amines [J].

Antilla, JC ;

Buchwald, SL .

ORGANIC LETTERS, 2001, 3 (13) :2077-2079

[3] α-Arylation of diethyl malonate via enolate with bases in a heterogeneous phase [J].

Aramendía, MA ;

Borau, V ;

Jiménez, C ;

Marinas, JM ;

Ruiz, JR ;

Urbano, FJ .

TETRAHEDRON LETTERS, 2002, 43 (15) :2847-2849

[4] Reaction of some 1,2-diaza-1,3-butadienes with activated methine compounds.: A straightforward entry to 1,4-dihydropyridazine, pyridazine, and 4,5(4H,5H)-cyclopropylpyrazole derivatives [J].

Attanasi, OA ;

Filippone, P ;

Fiorucci, C ;

Foresti, E ;

Mantellini, F .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9880-9887

[5] Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands [J].

Beare, NA ;

Hartwig, JF .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :541-555

[6]

Brunner H, 2000, EUR J ORG CHEM, V2000, P2119

[7] Control of stereochemistry in an intramolecular Diels-Alder reaction by the phenylsulfonyl group; an improved synthesis of pisiferol [J].

Bush, EJ ;

Jones, DW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (23) :3531-3536

[8] OXYGEN CARRIER AND REDOX PROPERTIES OF SOME NEUTRAL COBALT CHELATES - AXIAL AND IN-PLANE LIGAND EFFECTS [J].

CARTER, MJ ;

RILLEMA, DP ;

BASOLO, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (02) :392-400

[9] ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS - HIGHLY DIASTEREOSELECTIVE ALKYLATION OF CHIRAL 2-CYANO ESTERS [J].

CATIVIELA, C ;

DIAZDEVILLEGAS, MD ;

GALVEZ, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2497-2505

[10] SYNTHESIS AND PROPERTIES OF ENANTIOPURE BICYCLIC AMIDINES [J].

CONVERY, MA ;

DAVIS, AP ;

DUNNE, CJ ;

MACKINNON, JW .

TETRAHEDRON LETTERS, 1995, 36 (24) :4279-4282

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