Copper-Mediated N-Heteroarylation of Primary Sulfonamides: Synthesis of Mono-N-heteroaryl Sulfonamides

被引：85

作者：

Baffoe, Jonathan ^{[1
]}

Hoe, Madelene Y. ^{[1
]}

Toure, B. Barry ^{[1
]}

机构：

[1] Novartis Inst Biomed Res Inc, Oncol, Global Discovery Chem, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 07期

关键词：

CROSS-COUPLING REACTION; ARYL HALIDES; C-N; GOLDBERG REACTIONS; BOND FORMATION; ULLMANN; ACID; ARYLATION; AMIDATION; PALLADIUM;

D O I：

10.1021/ol100263r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the coupling of primary sulfonamides and various halogenated heterocyclic cores, with an emphasis on 2-heteroaryl halides, via copper catalysis. These studies enabled the synthesis of many new mono-N-heteroaryl sulfonamides. The electronic factors that influence the course of the reaction have also been Investigated.

引用

页码：1532 / 1535

页数：4

共 44 条

[1] Pyrrole-2-carboxylic acid as a ligand for the Cu-catalyzed reactions of primary anilines with aryl halides [J].

Altman, Ryan A. ;

Anderson, Kevin W. ;

Buchwald, Stephen L. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) :5167-5169

[2] 2-(Trimethylsilyl)ethanesulfonyl amide as a new ammonia equivalent for palladium-catalyzed amination of aryl halides [J].

Anjanappa, Prakash ;

Mullick, Dibakar ;

Selvakumar, Kumaravel ;

Sivakumar, Manickam .

TETRAHEDRON LETTERS, 2008, 49 (31) :4585-4587

[3] 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

[4] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[5] Palladium-catalyzed intermolecular coupling of aryl chlorides and sulfonamides under microwave irradiation [J].

Burton, G ;

Cao, P ;

Li, G ;

Rivero, R .

ORGANIC LETTERS, 2003, 5 (23) :4373-4376

[6] Palladium and copper-catalysed arylation reactions in the presence of water, with a focus on carbon-heteroatom bond formation [J].

Carril, Monica ;

SanMartin, Raul ;

Dominguez, Esther .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (04) :639-647

[7] New N- and O-arylations with phenylboronic acids and cupric acetate [J].

Chan, DMT ;

Monaco, KL ;

Wang, RP ;

Winters, MP .

TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936

[8] N-arylation of sulfonamidies on solid supports [J].

Combs, AP ;

Rafalski, M .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (01) :29-32

[9] Selected patented cross-coupling reaction technologies [J].

Corbet, Jean-Pierre ;

Mignani, Gerard .

CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710

[10] Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates [J].

Deng, James Z. ;

Paone, Daniel V. ;

Ginnetti, Anthony T. ;

Kurihara, Hideki ;

Dreher, Spencer D. ;

Weissman, Steven A. ;

Stauffer, Shaun R. ;

Burgey, Christopher S. .

ORGANIC LETTERS, 2009, 11 (02) :345-347

← 1 2 3 4 5 →