One-Pot Approach to 1,2-Disubstituted Indoles via Cu(II)-Catalyzed Coupling/Cyclization under Aerobic Conditions and Its Application for the Synthesis of Polycyclic Indoles

被引:70
作者
Gao, Jilong [1 ]
Shao, Yingying [1 ]
Zhu, Jiaoyan [1 ]
Zhu, Jiaqi [1 ]
Mao, Hui [1 ]
Wang, Xiaoxia [1 ]
Lv, Xin [1 ]
机构
[1] Zhejiang Normal Univ, Coll Chem & Life Sci, Dept Chem, Jinhua 321004, Peoples R China
基金
中国国家自然科学基金;
关键词
EFFICIENT SYNTHESIS; COUPLING REACTIONS; INTRAMOLECULAR CYCLIZATION; CATALYZED REACTIONS; MODULAR SYNTHESIS; FACILE SYNTHESIS; RING SYNTHESIS; N-ARYLATION; DERIVATIVES; INHIBITORS;
D O I
10.1021/jo501250u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A straightforward assembly of 1,2-disubstituted indoles has been developed through a Cu(II)-catalyzed domino coupling/cyclization process. Under aerobic conditions, a wide range of 1,2-disubstituted indole derivatives were efficiently and facilely synthesized from 2-alkynylanilines and boronic acids. 2-(2-Bromoaryl)-1-aryl-1H-indoles, which were selectively generated in one pot under the Cu catalysis, afforded the indolo[1,2-f]phenanthridines via Pd-catalyzed intramolecular direct C(sp(2))-H arylation. The one-pot tandem approaches to the polycyclic indole derivatives were also successfully achieved.
引用
收藏
页码:9000 / 9008
页数:9
相关论文
共 85 条
[1]   TiCl4/t-BuNH2-promoted hydroamination/annulation of δ-keto-acetylenes:: Synthesis of novel pyrrolo[1,2-a]indol-2-carbaldehydes [J].
Abbiati, Giorgio ;
Casoni, Alessandro ;
Canevari, Valentina ;
Nava, Donatella ;
Rossi, Elisabetta .
ORGANIC LETTERS, 2006, 8 (21) :4839-4842
[2]   General and efficient indole syntheses based on catalytic amination reactions [J].
Ackermann, L .
ORGANIC LETTERS, 2005, 7 (03) :439-442
[3]   Thieme Chemistry Journal Awardees - Where Are They Now? Palladium-Catalyzed N-Arylation-Hydroamination Sequence for the Synthesis of Indoles with Sterically Demanding N-Substituents [J].
Ackermann, Lutz ;
Sandmann, Rene ;
Kondrashov, Mikhail V. .
SYNLETT, 2009, (08) :1219-1222
[4]   Copper-Catalyzed N-Arylation/Hydroamin(d)ation Domino Synthesis of Indoles and its Application to the Preparation of a Chek1/KDR Kinase Inhibitor Pharmacophore [J].
Ackermann, Lutz ;
Barfuesser, Sebastian ;
Potukuchi, Harish K. .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (7-8) :1064-1072
[5]  
Akira T., 2000, J AM CHEM SOC, V122, P5662
[6]   Highly Efficient Route to Functionalized Tetrahydrocarbazoles Using a Tandem Cross-Metathesis/Intramolecular-Hydroarylation Sequence [J].
An, Xiao-Lei ;
Chen, Jia-Rong ;
Li, Chang-Feng ;
Zhang, Fu-Gen ;
Zou, You-Quan ;
Guo, Ying-Cen ;
Xiao, Wen-Jing .
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (10) :2258-2265
[7]   Copper-catalyzed coupling of arylboronic acids and amines [J].
Antilla, JC ;
Buchwald, SL .
ORGANIC LETTERS, 2001, 3 (13) :2077-2079
[8]   The copper-catalyzed N-arylation of indoles [J].
Antilla, JC ;
Klapars, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688
[9]   Synthesis and photovoltaic properties of novel organic sensitizers containing indolo[1,2-f]phenanthridine for solar cell [J].
Baik, Chul ;
Kim, Duckhyun ;
Kang, Moon-Sung ;
Song, Kihyung ;
Kang, Sang Ook ;
Ko, Jaejung .
TETRAHEDRON, 2009, 65 (27) :5302-5307
[10]   "On-Water," Microwave-Assisted, Pd-Catalyzed Synthesis of Indoles from 'mines and o-Difunctionalized Arenes [J].
Barluenga, Jose ;
Jimenez-Aquino, Agustin ;
Aznar, Fernando ;
Valdes, Carlos .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (38) :11707-11711