Iron-catalyzed deoxygenation and 2-sulfonylation of quinoline N-oxides by sodium sulfinates towards 2-sulfonyl quinolines

被引：23

作者：

Li, Ping ^{[1
]}

Jiang, Yangji ^{[1
]}

Li, Han ^{[2
]}

Dong, Wanrong ^{[1
]}

Peng, Zhihong ^{[1
]}

An, Delie ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha, Hunan, Peoples R China

[2] 3 Middle Sch Tianjin, Tianjin, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2018年 / 48卷 / 15期

关键词：

Iron catalysis; deoxygenation; 2-sulfonylation; quinoline N-oxides; sodium sulfinates; ONE-POT SYNTHESIS; C-H BORYLATION; BASE-FREE; MEDIATED SULFONYLATION; BOND FORMATION; METAL; ARYLATION; ACIDS; FUNCTIONALIZATION; ACTIVATION;

D O I：

10.1080/00397911.2018.1460670

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iron(III)-catalyzed protocol towards 2-sulfonyl quinolines from quinoline N-oxides and sodium sulfinates was herein illustrated. The general and direct option featured for high efficiency (up to 91% yields) and good functional compatibilities (27 examples) in the Fe(III)-catalysis. Moreover, free radical mechanism was proposed for the one-pot deoxygenation and sulfonylation reaction based on the results of the control reactions. GRAPHICAL ABSTRACT An novel reaction between quinoline N-oxides and sodium sulfinates for the synthesis of 2-sulfonyl quinolines was herein achieved by an iron(III)-catalyzed system. The general and direct transformation exhibited high efficiency (up to 91% yields) and good functionalgroups compatibilities (27 examples). Moreover, free radical mechanism was proposed for the one-pot deoxygenation and sulfonylation reaction based on the results of the control reactions. [GRAPHICS] .

引用

页码：1909 / 1918

页数：10

共 62 条

[1]

Andrews N. C. N., 1999, ENGL J MED, V341, P1986

[2] Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].

Baudoin, Olivier .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911

[3] Iron Catalysis in Organic Synthesis [J].

Bauer, Ingmar ;

Knoelker, Hans-Joachim .

CHEMICAL REVIEWS, 2015, 115 (09) :3170-3387

[4] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636

[5] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[6] Iron-Catalyzed Synthesis of Sulfur-Containing Heterocycles [J].

Bosset, Cyril ;

Lefebvre, Gauthier ;

Angibaud, Patrick ;

Stansfield, Ian ;

Meerpoel, Lieven ;

Berthelot, Didier ;

Guerinot, Amandine ;

Cossy, Janine .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (08) :4020-4036

[7] SYNTHESIS OF THE ELEMENTS IN STARS [J].

BURBIDGE, EM ;

BURBIDGE, GR ;

FOWLER, WA ;

HOYLE, F .

REVIEWS OF MODERN PHYSICS, 1957, 29 (04) :547-650

[8] Copper- catalyzed C5-selective thio/selenocyanation of 8-aminoquinolines [J].

Chen, Jichao ;

Wang, Tianyu ;

Wang, Tong ;

Lin, Aijun ;

Yao, Hequan ;

Xu, Jinyi .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (01) :130-134

[9] A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis [J].

Chen, Mark S. ;

White, M. Christina .

SCIENCE, 2007, 318 (5851) :783-787

[10] Catalytic Silylation of Unactivated C-H Bonds [J].

Cheng, Chen ;

Hartwig, John F. .

CHEMICAL REVIEWS, 2015, 115 (17) :8946-8975

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