Copper-catalyzed halogen exchange in aryl halides: An aromatic Finkelstein reaction

被引：394

作者：

Klapars, A ^{[1
]}

Buchwald, SL ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 50期

关键词：

D O I：

10.1021/ja028865v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A mild and general method for the conversion of aryl, heteroaryl, and vinyl bromides into the corresponding iodides was developed utilizing a catalyst system comprising 5 mol % of Cul and 10 mol % of a 1,2- or 1,3-diamine ligand. A variety of polar functional groups are tolerated, and even N-H containing substrates such as sulfonamides, amides, and indoles are compatible with the reaction conditions. Both the reaction rate and the equilibrium conversion of the aryl bromide depend on the choice of the halide salt and the solvent. The best results were obtained using Nal as the halide salt and dioxane, n-butanol, or n-pentanol as the solvents. Copyright © 2002 American Chemical Society.

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页码：14844 / 14845

页数：2

相关论文

共 30 条

[1] The copper-catalyzed N-arylation of indoles [J].

Antilla, JC ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688

[2] METAL IONS + COMPLEXES IN ORGANIC REACTIONS .I. SUBSTITUTION REACTIONS BETWEEN ARYL HALIDES + CUPROUS SALTS IN ORGANIC SOLVENTS [J].

BACON, RGR ;

HILL, HAO .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (MAR) :1097-+

[3] ACID-MEDIATED REACTION OF BIS(PYRIDINE)IODONIUM(I) TETRAFLUOROBORATE WITH AROMATIC-COMPOUNDS - A SELECTIVE AND GENERAL IODINATION METHOD [J].

BARLUENGA, J ;

GONZALEZ, JM ;

GARCIAMARTIN, MA ;

CAMPOS, PJ ;

ASENSIO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :2058-2060

[4] BIMETALLIC CATALYSIS - A NEW METHOD FOR THE ACTIVATION OF CHLOROARENES TOWARD PALLADIUM-CATALYZED COUPLING WITH OLEFINS [J].

BOZELL, JJ ;

VOGT, CE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2655-2657

[5] New single-step radioiodination technique for peptides: Cu(I)-catalyzed nucleophilic nonisotopic displacement reaction. Synthesis of radioiodinated deltorphin and dermorphin analogues [J].

Ceusters, M ;

Tourwe, D ;

Callaerts, J ;

Mertens, J ;

Peter, A .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (25) :8324-8326

[6]

CLARK JH, 1987, CHEM COMMUN, P1409

[7]

COHEN T, 1974, TETRAHEDRON LETT, P3555

[8] MECHANISMS AND MODELS FOR HOMOGENEOUS COPPER MEDIATED LIGAND-EXCHANGE REACTIONS OF THE TYPE - CUNU + ARX-]ARNU + CUX [J].

COUTURE, C ;

PAINE, AJ .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (01) :111-120

[9] Directed electrophilic cyclizations: Efficient methodology for the synthesis of fused polycyclic aromatics [J].

Goldfinger, MB ;

Crawford, KB ;

Swager, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (20) :4578-4593

[10] THE REPLACEMENT OF BROMINE BY CHLORINE IN AROMATIC COMPOUNDS [J].

HARDY, WB ;

FORTENBAUGH, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (07) :1716-1718