Rhodium(III)-catalyzed C-H alkynylation of azomethine ylides under mild conditions

被引:40
作者
Zhang, Xueyun [1 ,2 ]
Qi, Zisong [2 ]
Gao, Jian [1 ]
Li, Xingwei [2 ]
机构
[1] Qilu Univ Technol, Sch Chem & Pharmaceut Engn, Jinan 250353, Peoples R China
[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
关键词
CATALYZED DIRECT ALKYNYLATION; TERMINAL ALKYNES; BOND FORMATION; GOLD; ACTIVATION; CASCADE; 2-ALKYNYLBENZALDEHYDE; FUNCTIONALIZATION; ISOQUINOLINES; ALKENES;
D O I
10.1039/c4ob01596g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rh(III)-catalyzed efficient C-H alkynylation of azomethine imines with alkynylated hypervalent iodine is developed under mild conditions. A broad scope of azomethine imines and alkyne substrates is established. The azomethine acts as a masked aldehyde and circumvents its poor directing effect.
引用
收藏
页码:9329 / 9332
页数:4
相关论文
共 51 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[2]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[3]   "Two Functional Groups in One Package": Using Both Alkyne π-Bonds in Cascade Transformations [J].
Alabugin, Igor V. ;
Gold, Brian .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (16) :7777-7784
[4]   Ruthenium-Catalyzed Direct ortho-Alkynylation of Arenes with Chelation Assistance [J].
Ano, Yusuke ;
Tobisu, Mamoru ;
Chatani, Naoto .
SYNLETT, 2012, (19) :2763-2767
[5]   Synthesis of Triazolo Isoquinolines and Isochromenes from 2-Alkynylbenzaldehyde via Domino Reactions under Transition-Metal-Free Conditions [J].
Arigela, Rajesh K. ;
Sarnala, Srinivas ;
Mahar, Rohit ;
Shukla, Sanjeev K. ;
Kundu, Bijoy .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) :10476-10484
[6]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
[7]   Para-Selective Gold-Catalyzed Direct Alkynylation of Anilines [J].
Brand, Jonathan P. ;
Waser, Jerome .
ORGANIC LETTERS, 2012, 14 (03) :744-747
[8]   Direct Alkynylation of Thiophenes: Cooperative Activation of TIPS-EBX with Gold and Bronsted Acids [J].
Brand, Jonathan P. ;
Waser, Jerome .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7304-7307
[9]   Direct Alkynylation of Indole and Pyrrole Heterocycles [J].
Brand, Jonathan P. ;
Charpentier, Julie ;
Waser, Jerome .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9346-9349
[10]   Rhodium(III)-Catalyzed Annulation of Azomethine Ylides with Alkynes via CH Activation [J].
Chen, Yuye ;
Wang, Fen ;
Zhen, Wencui ;
Li, Xingwei .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (2-3) :353-359