Synthesis of 2-Aryl-3,4,5,6-tetrachloropyridines and 2,6-Diaryl-3,4,5-trichloropyridines by Site-Selective Suzuki-Miyaura Reactions of Pentachloropyridine

被引：20

作者：

Ehlers, Peter ^{[1
,2
]}

Reimann, Sebastian ^{[1
,2
]}

Erfle, Silke ^{[1
,2
]}

Villinger, Alexander ^{[1
]}

Langer, Peter ^{[1
,2
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany

来源：

SYNLETT | 2010年 / 10期

关键词：

catalysis; palladium; Suzuki-Miyaura reaction; pyridine; regioselectivity; CROSS-COUPLING REACTIONS; POLYHALOGENOAROMATIC COMPOUNDS; POLYCHLOROAROMATIC COMPOUNDS; 2-SUBSTITUTED PYRIDINES; CONTAINING HETEROCYCLES; SUBSTITUTED PYRIDINES; EFFICIENT SYNTHESIS; CONVENIENT ACCESS; BORONIC ACIDS; ARYL HALIDES;

D O I：

10.1055/s-0029-1219951

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first Suzuki-Miyaura reactions of pentachloropyridine are reported. The reaction with two equivalents of arylboronic acids gave 2,6-diaryl-3,4,5-trichloropyridines, while the reaction with one equivalent of arylboronic acid afforded 2-aryl-3,4,5,6-tetrachloropyridines. The one-pot reaction of pentachloropyridine with two different arylboronic acids resulted in the formation of 2,6-diaryl-3,4,5-trichloropyridines containing two different aryl groups. All reactions proceeded with very good site selectivity.

引用

页码：1528 / 1532

页数：5

共 52 条

[1] Synthesis of 2-substituted pyridines via a regiospecific alkylation, alkynylation, and arylation of pyridine N-oxides [J].

Andersson, Hans ;

Almqvist, Fredrik ;

Olsson, Roger .

ORGANIC LETTERS, 2007, 9 (07) :1335-1337

[2] Catalytic amination of 2-substituted pyridines with hydrazine derivatives [J].

Arterburn, JB ;

Rao, KV ;

Ramdas, R ;

Dible, BR .

ORGANIC LETTERS, 2001, 3 (09) :1351-1354

[3] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters [J].

Billingsley, Kelvin ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3358-3366

[4]

BINNS H, 1971, J CHEM SOC C, P1223

[5] Syntheses of substituted pyridines, quinolines and diazines via palladium-catalyzed cross-coupling of aryl Grignard reagents [J].

Bonnet, V ;

Mongin, F ;

Trécourt, F ;

Quéguiner, G ;

Knochel, P .

TETRAHEDRON, 2002, 58 (22) :4429-4438

[6] POLYHALOGENOAROMATIC COMPOUNDS .41. PHOTOCHEMICAL DEHALOGENATION AND ARYLATION REACTIONS OF POLYHALOGENOAROMATIC AND POLYHALOGENOHETEROAROMATIC COMPOUNDS [J].

BRATT, J ;

IDDON, B ;

MACK, AG ;

SUSCHITZKY, H ;

TAYLOR, JA ;

WAKEFIELD, BJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (02) :648-656

[7] Palladium-catalyzed carbonylative cross-coupling reactions of pyridine halides and aryl boronic acids:: a convenient access to α-pyridyl ketones [J].

Couve-Bonnaire, S ;

Carpentier, JF ;

Mortreux, A ;

Castanet, Y .

TETRAHEDRON LETTERS, 2001, 42 (22) :3689-3691

[8]

Dang T.T., 2009, Adv. Synth. Catal, V351, P1595

[9]

Dang TT., 2008, ADV SYNTH CATAL, V350, P2109

[10] Regioselective Suzuki cross-coupling reactions of 2,3,4,5-tetrabromo-1-methylpyrrole [J].

Dang, Tung T. ;

Ahmad, Rasheed ;

Dang, Tuan T. ;

Reinke, Helmut ;

Langer, Peter .

TETRAHEDRON LETTERS, 2008, 49 (10) :1698-1700

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