Pd-Catalyzed Oxidative Coupling of Enamides and Alkynes for Synthesis of Substituted Pyrroles

被引:133
作者
Zhao, Mi-Na [1 ]
Ren, Zhi-Hui [1 ]
Wang, Yao-Yu [1 ]
Guan, Zheng-Hui [1 ]
机构
[1] NW Univ Xian, Dept Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol Chem, Minist Educ, Xian 710069, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H BONDS; POLYSUBSTITUTED PYRROLES; INTRAMOLECULAR ADDITION; EFFICIENT SYNTHESIS; TERTIARY ENAMIDES; TERMINAL ALKYNES; RUTHENIUM; CYCLOADDITION; ACTIVATION; INDOLES;
D O I
10.1021/ol403517p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and efficient palladium(II)-catalyzed alkenyl C-H activation oxidative annulation of enamides with alkynes for the synthesis of substituted pyrroles has been developed. The reaction tolerates a wide range of functional groups and is a reliable method for the synthesis of triaryl-substituted pyrroles in high yields.
引用
收藏
页码:608 / 611
页数:4
相关论文
共 75 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]   Cationic Ruthenium(II) Catalysts for Oxidative C-H/N-H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water [J].
Ackermann, Lutz ;
Lygin, Alexander V. .
ORGANIC LETTERS, 2012, 14 (03) :764-767
[3]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
[4]   A New Pyrrole Synthesis via Silver(I)-Catalyzed Cycloaddition of Vinylogous Diazoester and Nitrile [J].
Billedeau, Roland J. ;
Klein, Klara R. ;
Kaplan, Daniel ;
Lou, Yan .
ORGANIC LETTERS, 2013, 15 (07) :1421-1423
[5]   Enamides: valuable organic substrates [J].
Carbery, David R. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (19) :3455-3460
[6]   N,N′-Dioxide-Cu(OTf)2 Complex Catalyzed Highly Enantioselective Amination Reaction of N-Acetyl Enamide [J].
Chang, Lu ;
Kuang, Yulong ;
Qin, Bo ;
Zhou, Xin ;
Liu, Xiaohua ;
Lin, Lili ;
Feng, Xiaoming .
ORGANIC LETTERS, 2010, 12 (10) :2214-2217
[7]   2,4-vs 3,4-Disubsituted Pyrrole Synthesis Switched by Copper and Nickel Catalysts [J].
Chen, Feng ;
Shen, Tao ;
Cui, Yuxin ;
Jiao, Ning .
ORGANIC LETTERS, 2012, 14 (18) :4926-4929
[8]   Synthesis of N-(2-Pyridyl)indoles via Pd(II)-Catalyzed Oxidative Coupling [J].
Chen, Jinlei ;
Pang, Qingyu ;
Sun, Yanbo ;
Li, Xingwei .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) :3523-3526
[9]   Palladium-Catalyzed Oxidative Carbonylation of the Alkenyl C-H Bonds of Enamides: Synthesis of 1,3-Oxazin-6-ones [J].
Chen, Ming ;
Ren, Zhi-Hui ;
Wang, Yao-Yu ;
Guan, Zheng-Hui .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) :14196-14199
[10]   α-Palladation of Imines as Entry to Dehydrogenative Heck Reaction: Aerobic Oxidative Cyclization of N-Allylimines to Pyrroles [J].
Chen, Zhiyuan ;
Lu, Beili ;
Ding, Zhenhua ;
Gao, Ke ;
Yoshikai, Naohiko .
ORGANIC LETTERS, 2013, 15 (08) :1966-1969