A new strategy for the synthesis of benzylic sulfonamides: Palladium-catalyzed arylation and sulfonamide metathesis

被引：26

作者：

Grimm, Jonathan B. ^{[1
]}

Katcher, Matthew H. ^{[1
]}

Witter, David J. ^{[1
]}

Northrup, Alan B. ^{[1
]}

机构：

[1] Merck Res Labs, Dept Drug Design & Optimizat, Boston, MA 02115 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 21期

关键词：

D O I：

10.1021/jo701431j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An efficient two-step strategy has been developed to access diversely functionalized benzylic sulfonamides. Execution of this strategy required the development of two reaction methods: the palladium-catalyzed cross-coupling of aryl halides with CH-acidic methanesulfonamides and a metathesis reaction between the resulting alpha-arylated sulfonamides and diverse amines. The broad scope of the cross-coupling process combined with a versatile sulfonamide metathesis constitutes an efficient strategy for the synthesis of various benzylic sulfonamides.

引用

页码：8135 / 8138

页数：4

共 36 条

[1]

ABDELLAOUI H, 1995, SYNTHETIC COMMUN, V25, P1301

[2] Asymmetric arylation of ketone enolates [J].

Ahman, J ;

Wolfe, JP ;

Troutman, MV ;

Palucki, M ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1918-1919

[3] BASIN MODELS - GENERAL-CIRCULATION OF REGIONS OF THE WORLD OCEAN [J].

ANDERSON, D .

DYNAMICS OF ATMOSPHERES AND OCEANS, 1979, 3 (2-4) :345-371

[4] 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

[5] Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands [J].

Beare, NA ;

Hartwig, JF .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :541-555

[6] Palladium-catalyzed intramolecular α-arylation of sulfoximines [J].

Bolm, C ;

Okamura, H ;

Verrucci, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) :444-450

[7] Palladium-catalyzed α-arylation of sulfoximines [J].

Cho, GY ;

Bolm, C .

ORGANIC LETTERS, 2005, 7 (07) :1351-1354

[8] Palladium-catalyzed intermolecular α-arylation of N-protected 2-piperidinones [J].

Cossy, J ;

de Filippis, A ;

Pardo, DG .

ORGANIC LETTERS, 2003, 5 (17) :3037-3039

[9] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].

Culkin, DA ;

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245

[10] Synthesis, characterization, and reactivity of arylpalladium cyanoalkyl complexes:: Selection of catalysts for the α-arylation of nitriles [J].

Culkin, DA ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) :9330-9331

← 1 2 3 4 →