Copper-catalyzed tandem oxidative cyclization of cinnamamides with benzyl hydrocarbons through cross-dehydrogenative coupling

被引：120
作者：
Zhou, Shi-Liu
Guo, Li-Na
Wang, Shun
Duan, Xin-Hua [1 ]
机构：
[1] Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 27期
基金：
中国国家自然科学基金;
关键词：
SP(3) C-H; CARBON-HYDROGEN BONDS; 1,3-DICARBONYL COMPOUNDS; ACTIVATED ALKENES; ALLYLIC ALKYLATION; SIMPLE ALKANES; FUNCTIONALIZATION; CDC; OXINDOLES; ACRYLAMIDES;
D O I：
10.1039/c4cc00637b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The copper-catalyzed tandem oxidative cyclization of cinnamamides with benzyl hydrocarbons through the direct cross-dehydrogenative coupling of sp(3) and sp(2) C-H bonds has been developed. Satisfactorily, ethers, alcohols and alkanes could also be used instead of benzyl hydrocarbons in this transformation, which allows rapid access to diverse dihydroquinolinones in one step.
引用
收藏
页码：3589 / 3591
页数：3
相关论文
共 55 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]   Direct Selective Oxidative Cross-Coupling of Simple Alkanes with Heteroarenes [J].
Antonchick, Andrey P. ;
Burgmann, Lars .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) :3267-3271
[3]   Copper-Catalyzed Cross-Dehydrogenative Coupling (CDC) of Alkynes and Benzylic C-H Bonds [J].
Correia, Camille A. ;
Li, Chao-Jun .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (09) :1446-1450
[4]   Ruthenium-catalyzed oxidative cross-coupling of chelating arenes and cycloalkanes [J].
Deng, Guojun ;
Zhao, Liang ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (33) :6278-6282
[5]   Coupling of Nitrogen Heteroaromatics and Alkanes without Transition Metals: A New Oxidative Cross-Coupling at C-H/C-H Bonds [J].
Deng, Guojun ;
Ueda, Kirika ;
Yanagisawa, Shuichi ;
Itami, Kenichiro ;
Li, Chao-Jun .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (02) :333-337
[6]   Reversibility in Lewis-acid promoted reactions of N-arylcinnamamides [J].
Elliott, MC ;
Wordingham, SV .
SYNLETT, 2004, (05) :898-900
[7]   A Metal-Free Oxidative Esterification of the Benzyl C?H Bond [J].
Feng, Jie ;
Liang, Shuai ;
Chen, Shan-Yong ;
Zhang, Ji ;
Fu, Song-Sen ;
Yu, Xiao-Qi .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (07) :1287-1292
[8]   Hydrogen abstraction and electron transfer with aminoxyl radicals: Synthetic and mechanistic issues [J].
Galli, Carlo ;
Gentili, Patrizia ;
Lanzalunga, Osvaldo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) :4790-4796
[9]   The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].
Girard, Simon A. ;
Knauber, Thomas ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100
[10]   Four Tandem C-H Activations: A Sequential C-C and C-O Bond Making via a Pd-Catalyzed Cross Dehydrogenative Coupling (CDC) Approach [J].
Guin, Srimanta ;
Rout, Saroj Kumar ;
Banerjee, Arghya ;
Nandi, Shyamapada ;
Patel, Bhisma K. .
ORGANIC LETTERS, 2012, 14 (20) :5294-5297
123456