2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Mediated C(sp2)-C(sp3) Cross-Dehydrogenative Coupling Reaction: α-Alkylation of Push-Pull Enamines and α-Oxo Ketene Dithioacetals

被引：20

作者：

Cheng, Dongping ^{[1
]}

Wu, Lijun ^{[1
]}

Deng, Zhiteng ^{[1
]}

Xu, Xiaoliang ^{[2
]}

Yan, Jizhong ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China

[2] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 24期

关键词：

C-H activation; cross-coupling; DDQ; dehydrogenation; 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; metal-free reaction; C-H ACTIVATION; 1,3-DICARBONYL COMPOUNDS; CYCLIC ENAMINONES; BOND FORMATION; CDC; PROPARGYLATION; ARYLATION;

D O I：

10.1002/adsc.201700853

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel, metal-free cross-dehydrogenative coupling (CDC) reaction of C(sp(2))-H bonds of enamines and alpha-oxo ketene dithioacetals with C(sp(3))-H bonds of 1,3-diarylpropenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is reported. The alpha-alkylation products are obtained with moderate to good yields. The method provides an efficient and alternative strategy for the synthesis of the corresponding products.

引用

页码：4317 / 4321

页数：5

共 34 条

[1] CDC Reactions of N-Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: C-H Activation under Aerobic Conditions [J].

Alagiri, Kaliyamoorthy ;

Devadig, Pradeep ;

Prabhu, Kandikere R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (17) :5160-5164

[2] Propargylation of 1,3-dicarbonyl compounds with 1,3-diarylpropynes via oxidative cross-coupling between sp3 C-H and sp3 C-H [J].

Cheng, Dongping ;

Bao, Weiliang .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6881-6883

[3] Highly efficient metal-free cross-coupling by C-H activation between allylic and active methylenic compounds promoted by DDQ [J].

Cheng, Dongping ;

Bao, Weiliang .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) :1263-1266

[4] CDC Reaction and Subsequent Cyclization for the Synthesis of 2-Hydroxy-3-alkyl-1,4-naphthoquinones and Pyranonaphthoquinones [J].

Cheng, Dongping ;

Wu, Lijun ;

Lv, Huawei ;

Xu, Xiaoliang ;

Yan, Jizhong .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (03) :1610-1617

[5] Propargylation of 1,3-dicarbonyl compounds catalyzed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and sodium nitrite in the presence of molecular oxygen and formic acid [J].

Cheng, Dongping ;

Zhou, Xiayi ;

Xu, Xiaoliang ;

Yan, Jizhong .

RSC ADVANCES, 2016, 6 (57) :52459-52463

[6] The oxidative coupling of benzylic compounds catalyzed by 2,3-dichloro-5,6-dicyano-benzoquinone and sodium nitrite using molecular oxygen as a co-oxidant [J].

Cheng, Dongping ;

Yuan, Kun ;

Xu, Xiaoliang ;

Yan, Jizhong .

TETRAHEDRON LETTERS, 2015, 56 (13) :1641-1644

[7]

Corey E. J., 1989, the Logic of Chemical Synthesis

[8] ALPHA-OXO KETENE DITHIOACETALS AND RELATED-COMPOUNDS - VERSATILE 3-CARBON SYNTHONS [J].

DIETER, RK .

TETRAHEDRON, 1986, 42 (12) :3029-3096

[9] Recent developments in the chemistry of enaminones [J].

Elassar, AZA ;

El-Khair, AA .

TETRAHEDRON, 2003, 59 (43) :8463-8480

[10]

Girard S. A., 2014, ANGEW CHEM, V126, P76

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