Role of copper species in the oxidative dimerization of arylboronic acids:: Synthesis of symmetrical biaryls

被引：130

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：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 26期

关键词：

D O I：

10.1021/jo034680a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Certain Cu(I) and Cu(II) salts are able to mediate the dimerization of arylboronic acids in DMF. They provide the corresponding symmetrical biaryls in moderate to very good yields. It is possible to run the reaction catalytically under an oxygen atmosphere without a significant loss of yields.

引用

页码：10130 / 10134

页数：5

共 39 条

[1] Copper-mediated cross-coupling of organostannanes with organic iodides at or below room temperature [J].

Allred, GD ;

Liebeskind, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) :2748-2749

[2]

COHEN T, 1974, TETRAHEDRON LETT, P3555

[3] An efficient diamine copper complex-catalyzed coupling of arylboronic acids with imidazoles [J].

Collman, JP ;

Zhong, M .

ORGANIC LETTERS, 2000, 2 (09) :1233-1236

[4] Solid supported aryl/heteroaryl C-N cross-coupling reactions. [J].

Combs, AP ;

Saubern, S ;

Rafalski, M ;

Lam, PYS .

TETRAHEDRON LETTERS, 1999, 40 (09) :1623-1626

[5] Electroreductive coupling of organic halides in alcoholic solvents. An example: The electrosynthesis of biaryls catalysed by nickel-2,2' bipyridine complexes. [J].

Courtois, V ;

Barhdadi, R ;

Troupel, M ;

Perichon, J .

TETRAHEDRON, 1997, 53 (34) :11569-11576

[6] Generation of aryl radicals from arylboronic acids by manganese(III) acetate:: Synthesis of biaryls and heterobiaryls [J].

Demir, AS ;

Reis, Ö ;

Emrullahoglu, M .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :578-580

[7]

DHAR SK, 1984, J CHEM SOC CHEM COMM, P8

[8] ANOMALY IN PALLADIUM-CATALYZED PHENYLETHYNYLATION OF 2,2'-DIHALOBIPHENYLS - FORMATION OF ALKYLIDENEFLUORENES [J].

DOUGHERTY, TK ;

LAU, KSY ;

HEDBERG, FL .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) :5273-5280

[9] Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine [J].

Evans, DA ;

Katz, JL ;

West, TR .

TETRAHEDRON LETTERS, 1998, 39 (19) :2937-2940

[10] Homocoupling of alkyl-, alkenyl-, and arylboronic acids [J].

Falck, JR ;

Mohapatra, S ;

Bondlela, M ;

Venkataraman, SK .

TETRAHEDRON LETTERS, 2002, 43 (45) :8149-8151

← 1 2 3 4 →