α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

被引：54

作者：

Caiuby, Clarice A. D. ^{[1
]}

de Jesus, Matheus P. ^{[1
]}

Burtoloso, Antonio C. B. ^{[1
]}

机构：

[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP, Brazil

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 11期

基金：

巴西圣保罗研究基金会;

关键词：

HIGHLY SUBSTITUTED PYRROLES; DIAZO OXIME ETHERS; C-H ANNULATION; TITANIUM TETRACHLORIDE; ASYMMETRIC-SYNTHESIS; OXOSULFONIUM YLIDES; EXPEDIENT SYNTHESIS; DIVERGENT SYNTHESIS; CATALYZED REACTIONS; ORGANIC-SYNTHESIS;

D O I：

10.1021/acs.joc.0c00833

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate alpha-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl](2) (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding beta-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).

引用

页码：7433 / 7445

页数：13

共 100 条

[11] Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles [J].

Chuprakov, Stepan ;

Hwang, Frank W. ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) :4757-4759

[12] Stereoselective 1,3-Insertions of Rhodium(II) Azavinyl Carbenes [J].

Chuprakov, Stepan ;

Worrell, Brady T. ;

Selander, Nicklas ;

Sit, Rakesh K. ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (01) :195-202

[13] Transannulation of 1-Sulfonyl-1,2,3-triazoles with Heterocumulenes [J].

Chuprakov, Stepan ;

Kwok, Sen Wai ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (12) :4652-4655

[14] Catalytic Asymmetric C-H Insertions of Rhodium(II) Azavinyl Carbenes [J].

Chuprakov, Stepan ;

Malik, Jamal A. ;

Zibinsky, Mikhail ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (27) :10352-10355

[15] Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles [J].

Davies, Huw M. L. ;

Alford, Joshua S. .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (15) :5151-5162

[16] Nucleophilic Nitrenoids Through π-Acid Catalysis: Providing a Common Basis for Rapid Access into Diverse Nitrogen Heterocycles [J].

Davies, Paul W. ;

Garzon, Miguel .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (08) :694-708

[17] Intermolecular and Selective Synthesis of 2,4,5-Trisubstituted Oxazoles by a Gold-Catalyzed Formal [3+2] Cycloaddition [J].

Davies, Paul W. ;

Cremonesi, Alex ;

Dumitrescu, Lidia .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) :8931-8935

[18] Taming Hazardous Chemistry in Flow: The Continuous Processing of Diazo and Diazonium Compounds [J].

Deadman, Benjamin J. ;

Collins, Stuart G. ;

Maguire, Anita R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (06) :2298-2308

[19] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].

DOYLE, MP .

CHEMICAL REVIEWS, 1986, 86 (05) :919-939

[20] Electrosynthesis of Substituted 1H-Indoles from o-Nitrostyrenes [J].

Du, Peng ;

Brosmer, Jonathan L. ;

Peters, Dennis G. .

ORGANIC LETTERS, 2011, 13 (15) :4072-4075

← 1 2 3 4 5 6 7 8 9 10 →