Access to Indenones by Rhodium(III)-Catalyzed C-H Annulation of Arylnitrones with Internal Alkynes

被引:133
作者
Qi, Zisong [1 ,2 ]
Wang, Mei [2 ]
Li, Xingwei [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
关键词
N BOND FORMATION; CATALYZED ANNULATION; EFFICIENT SYNTHESIS; ARYL; CYCLIZATION; ACTIVATION; ARENES; FUNCTIONALIZATION; LIGANDS; ISOCYANATES;
D O I
10.1021/ol4025309
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under redox-neutral conditions, rhodium(III)-catalyzed C-H annulation of N-tert-butyl-alpha-arylnitrones with internal alkynes has been realized for the synthesis of indenones under mild conditions. This reaction proceeded in moderate to high yields and with good functional group tolerance.
引用
收藏
页码:5440 / 5443
页数:4
相关论文
共 71 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]   2-ARYLINDENES AND 2-ARYLINDENONES - MOLECULAR-STRUCTURES AND CONSIDERATIONS IN THE BINDING ORIENTATION OF UNSYMMETRICAL NONSTEROIDAL LIGANDS TO THE ESTROGEN-RECEPTOR [J].
ANSTEAD, GM ;
WILSON, SR ;
KATZENELLENBOGEN, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (09) :2163-2171
[4]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[5]   Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates [J].
Chan, Wai-Wing ;
Lo, Siu-Fung ;
Zhou, Zhongyuan ;
Yu, Wing-Yiu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13565-13568
[6]   Rhodium-Catalyzed Direct Annulation of Aldehydes with Alkynes Leading to Indenones: Proceeding through in Situ Directing Group Formation and Removal [J].
Chen, Shuyou ;
Yu, Jintao ;
Jiang, Yan ;
Chen, Fan ;
Cheng, Jiang .
ORGANIC LETTERS, 2013, 15 (18) :4754-4757
[7]   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
[8]   Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Kwak, Jaesung ;
Chang, Sukbok .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083
[9]   A catalytic enantioselective synthesis of the endothelin receptor antagonists SB-209670 and SB-217242. A base-catalyzed stereospecific formal 1,3-hydrogen transfer of a chiral 3-arylindenol [J].
Clark, WM ;
Tickner-Eldridge, AM ;
Huang, GK ;
Pridgen, LN ;
Olsen, MA ;
Mills, RJ ;
Lantos, I ;
Baine, NH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4550-4551
[10]   Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].
Colby, Denise A. ;
Tsai, Andy S. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825