Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides

被引：204

作者：

Shavnya, Andrei ^{[1
]}

Coffey, Steven B. ^{[1
]}

Smith, Aaron C. ^{[1
]}

Mascitti, Vincent ^{[1
]}

机构：

[1] Pfizer Inc, Groton, CT 06340 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 24期

关键词：

SULFUR-DIOXIDE;

D O I：

10.1021/ol403072r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel palladium-catalyzed sulfination of aryl and heteroaryl halides is described. This reaction operates under mild conditions and provides access to a wide range of aryl and heteroaryl sulfinates, a useful and versatile class of synthetic intermediates. Capitalizing on this sulfination reaction, one-pot protocols allowing direct access to sulfones and sulfonamides have also been developed. The practicality of these transformations is illustrated with the parallel synthesis of analogues of the drug Viagra.

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页码：6226 / 6229

页数：4

相关论文

共 13 条

[1] A mild, convenient synthesis of sulfinic acid salts and sulfonamides from alkyl and aryl halides [J].

Baskin, JM ;

Wang, ZY .

TETRAHEDRON LETTERS, 2002, 43 (47) :8479-8483

[2] REACTIONS OF ETHYLENE OXIDES .2. REACTIONS WITH THIOAMIDES, THIOLS, AND INORGANIC SULPHUR SALTS [J].

CULVENOR, CCJ ;

DAVIES, W ;

HEATH, NS .

JOURNAL OF THE CHEMICAL SOCIETY, 1949, (FEB) :278-282

[3] Synthesis of Aryl Sulfonamides via Palladium-Catalyzed Chlorosulfonylation of Arylboronic Acids [J].

DeBergh, J. Robb ;

Niljianskul, Nootaree ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (29) :10638-10641

[4] O AND S METHYLATION OF AMBIDENT P-TOLUENESULFINATE ANION [J].

MEEK, JS ;

FOWLER, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (09) :3422-&

[5] Palladium-Catalyzed Aminosulfonylation of Aryl Halides [J].

Nguyen, Bao ;

Emmett, Edward J. ;

Willis, Michael C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (46) :16372-16373

[6] Palladium-catalyzed synthesis of sulfinic acids from aryldiazonium tetrafluoroborates, sulfur dioxide and hydrogen [J].

Pelzer, G ;

Keim, W .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 139 (2-3) :235-238

[7] Catalytic transformations of sulfur dioxide into organic sulfur compounds [J].

Pelzer, G ;

Herwig, J ;

Keim, W ;

Goddard, R .

RUSSIAN CHEMICAL BULLETIN, 1998, 47 (05) :904-913

[8] REDUCTIVE FORMYLATION OF AROMATIC HALIDES UNDER LOW-CARBON MONOXIDE PRESSURE CATALYZED BY TRANSITION-METAL COMPOUNDS [J].

PRIBAR, I ;

BUCHMAN, O .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :4009-4011

[9] One-pot three-component sulfone synthesis exploiting palladium-catalysed aryl halide aminosulfonylation [J].

Richards-Taylor, Charlotte S. ;

Blakemore, David C. ;

Willis, Michael C. .

CHEMICAL SCIENCE, 2014, 5 (01) :222-228

[10]

Schubart R., 2000, ULLMANNS ENCYCLOPEDI, P677