Mild Pd-Catalyzed N-Arylation of Methanesulfonamide and Related Nucleophiles: Avoiding Potentially Genotoxic Reagents and Byproducts

被引：105

作者：

Rosen, Brandon R. ^{[1
]}

Ruble, J. Craig ^{[1
]}

Beauchamp, Thomas J. ^{[1
]}

Navarro, Antonio ^{[1
]}

机构：

[1] Eli Lilly & Co, Lilly Corp Ctr, Indianapolis, IN 46285 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 10期

关键词：

CROSS-COUPLING REACTIONS; C-N; ARYL CHLORIDES; PHOSPHINE-LIGANDS; PALLADIUM; SULFONAMIDES; AMINATION; HALIDES; COMPLEXES; BROMIDES;

D O I：

10.1021/ol200660s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient, general, and high yielding Pd-catalyzed cross-coupling of methanesulfonamide with aryl bromides and chlorides Is reported. The use of this method eliminates concern over genotoxic impurities that can arise when an aniline is reacted with methanesulfonyl chloride. The application of this method to the synthesis of dofetilide is also reported.

引用

页码：2564 / 2567

页数：4

共 34 条

[31]

Ullmann, 1913, LIEBIGS ANN CHEM, V399, P330

[32] Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene) [J].

Viciu, MS ;

Navarro, O ;

Germaneau, RF ;

Kelly, RA ;

Sommer, W ;

Marion, N ;

Stevens, ED ;

Cavallo, L ;

Nolan, SP .

ORGANOMETALLICS, 2004, 23 (07) :1629-1635

[33] Intramolecular palladium-catalyzed aryl amination and aryl amidation [J].

Wolfe, JP ;

Rennels, RA ;

Buchwald, SL .

TETRAHEDRON, 1996, 52 (21) :7525-7546

[34] Palladium-catalyzed intermolecular coupling of aryl halides and amides [J].

Yin, JJ ;

Buchwald, SL .

ORGANIC LETTERS, 2000, 2 (08) :1101-1104

← 1 2 3 4 →