Manganese(III) acetate-mediated oxidative coupling of phenylhydrazines with furan and thiophene:: a novel method for hetero biaryl coupling

被引：43

作者：

Demir, AS ^{[1
]}

Reis, Ö ^{[1
]}

Emrullahoglu, M ^{[1
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

来源：

TETRAHEDRON | 2002年 / 58卷 / 40期

关键词：

arylcoupling; thiophene; furan; manganese(III) acetate;

D O I：

10.1016/S0040-4020(02)01001-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient new method for the arylation of furan and thiophene with arylhydrazine and manganese(III) acetate is described. Oxidation of arylhydrazines with Mn(III) acetate in furan or thiophene affords the corresponding 2-aryl-substituted furans and thiophenes in good yield using commercially available materials; access to 2-substituted heterobiaryls works selectively, and coupling occurs with loss of the hydrazine moiety. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：8055 / 8058

页数：4

共 39 条

[1] PHOTOCHEMICAL-SYNTHESIS OF PHENYL-2-THIENYL DERIVATIVES [J].

ANTONIOLETTI, R ;

DAURIA, M ;

DONOFRIO, F ;

PIANCATELLI, G ;

SCETTRI, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (10) :1755-1758

[2] OXIDATION OF HYDRAZINE DERIVATIVES .I. OXIDATION OF PHENYLHYDRAZINE WITH LEAD TETRA-ACETATE [J].

AYLWARD, JB .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (12) :1663-&

[3]

BARAKAT Z, 1956, J CHEM SOC, P4685

[4] PHASE-TRANSFER-CATALYZED GOMBERG-BACHMANN SYNTHESIS OF UNSYMMETRICAL BIARENES - A SURVEY OF CATALYSTS AND SUBSTRATES [J].

BEADLE, JR ;

KORZENIOWSKI, SH ;

ROSENBERG, DE ;

GARCIASLANGA, BJ ;

GOKEL, GW .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) :1594-1603

[5] COMBINED DIRECTED METALATION - CROSS COUPLING STRATEGIES - A REGIOSPECIFIC ROUTE TO HETERORING-ANNELATED ORTHO-NAPHTHOQUINONES AND A SHORT SYNTHESIS OF BETA-LAPACHONE [J].

BRANDAO, MAF ;

DEOLIVEIRA, AB ;

SNIECKUS, V .

TETRAHEDRON LETTERS, 1993, 34 (15) :2437-2440

[6] PRODUCTION OF A PYRROLE ANTIBIOTIC BY A MARINE BACTERIUM [J].

BURKHOLDER, PR ;

PFISTER, RM ;

LEITZ, FH .

APPLIED MICROBIOLOGY, 1966, 14 (04) :649-+

[7] CONVENIENT PREPARATIONS OF DEUTERIUM-SUBSTITUTED FURAN-2-CARBOXYLIC THIOPHEN-2-CARBOXYLIC AND N-METHYLPYRROLE-2-CARBOXYLIC ACIDS, AND OF TETRADEUTERIOFURAN [J].

CHADWICK, DJ ;

CHAMBERS, J ;

MEAKINS, GD ;

SNOWDEN, RL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (03) :201-202

[8] ISOFLAVONOIDS .I. SOME NEW CONSTITUENTS OF PTEROCARPUS INDICUS HEARTWOOD [J].

COOKE, RG ;

RAE, ID .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1964, 17 (03) :379-&

[9] Butenolide annelation using a manganese(III) oxidation. A synthesis of chromolaenin (Laevigatin) [J].

Demir, AS ;

Gercek, Z ;

Duygu, N ;

Igdir, AC ;

Reis, O .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1999, 77 (08) :1336-1339

[10] Manganese(III) acetate-mediated oxidative coupling of phenylhydrazines with benzene:: a novel method for biaryl coupling [J].

Demir, AS ;

Reis, Ö ;

Özgül-Karaaslan, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (22) :3042-3045

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