Palladium-Catalyzed C-S Activation/Aryne Insertion/Coupling Sequence: Synthesis of Functionalized 2-Quinolinones

被引：82

作者：

Dong, Ying ^{[1
]}

Liu, Bangyu ^{[1
]}

Chen, Peng ^{[1
]}

Liu, Qun ^{[1
]}

Wang, Mang ^{[1
]}

机构：

[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 13期

关键词：

annulation; arynes; CS activation; heterocycles; synthetic methods; KETENE DITHIOACETALS; STEREOSELECTIVE-SYNTHESIS; BOND ACTIVATION; SULFIDES; BENZYNE; ARYNES; DERIVATIVES; CYCLIZATION; THIOESTERS; ANNULATION;

D O I：

10.1002/anie.201310340

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The insertion of an aryne into a CS bond can suppress the addition of an Snucleophile to the aryne in the presence of palladium. Catalyzed by Pd(OAc)(2), a wide range of -carbamoyl ketene dithioacetals readily react with arynes to selectively afford functionalized 2-quinolinones in high yields under neutral reaction conditions by a CS activation/aryne insertion/intramolecular coupling sequence. The attractive feature of the new strategy also lies in the versatile transformations of the alkythio-substituted quinolinone products.

引用

页码：3442 / 3446

页数：5

共 56 条

[41] Carbocyclization of unsaturated thioesters under palladium catalysis [J].

Thottumkara, Arun P. ;

Kurokawa, Toshiki ;

Du Bois, J. .

CHEMICAL SCIENCE, 2013, 4 (06) :2686-2689

[42] A new paradigm for carbon-carbon bond formation: Aerobic, copper-templated cross-coupling [J].

Villalobos, Janette M. ;

Srogl, Jiri ;

Liebeskind, Lanny S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (51) :15734-+

[43] Transition-metal mediated carbon-sulfur bond activation and transformations [J].

Wang, Liandi ;

He, Wei ;

Yu, Zhengkun .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (02) :599-621

[44] Tandem [4+1+1] annulation and metal-free aerobic oxidative aromatization: straightforward synthesis of highly substituted phenols from one aldehyde and two ketones [J].

Wang, Mang ;

Fu, Zhenqian ;

Feng, Hui ;

Dong, Ying ;

Liu, Jun ;

Liu, Qun .

CHEMICAL COMMUNICATIONS, 2010, 46 (47) :9061-9063

[45] Synthesis of β-, γ-, and δ-Lactams via Pd(II)-Catalyzed C-H Activation Reactions [J].

Wasa, Masayuki ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (43) :14058-+

[46] NOVEL REACTIONS OF BENZYNE WITH ACETYLENIC ETHERS [J].

WASSERMAN, HH ;

FERNANDEZ, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (19) :5322-+

[47]

Worlikar SA, 2011, CURR ORG CHEM, V15, P3214

[48] In Situ Generation of PhI+CF3 and Transition-Metal-Free Oxidative sp2 CH Trifluoromethylation [J].

Xu, Cong ;

Liu, Jingxin ;

Ming, Wenbo ;

Liu, Yingjie ;

Liu, Jun ;

Wang, Mang ;

Liu, Qun .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (28) :9104-9109

[49] Intramolecular Anodic Olefin Coupling Reactions: Use of the Reaction Rate To Control Substrate/Product Selectivity [J].

Xu, Hai-Chao ;

Moeller, Kevin D. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (43) :8004-8007

[50]

XU HC, 2010, ANGEW CHEM, V122, P8176

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