One-Pot Synthesis of Decahydropyrene via Tandem C-H Activation/Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition

被引:14
作者
Lin, Hui [1 ]
Dong, Lin [1 ]
机构
[1] Sichuan Univ, West China Sch Pharm, Educ Minist, Key Lab Drug Targeting & Drug Delivery Syst, Chengdu 610041, Peoples R China
关键词
INTERNAL ALKYNES; POLYHETEROAROMATIC COMPOUNDS; CATALYZED ANNULATION; CARBOXYLIC-ACIDS; DIRECTING GROUPS; BOND ACTIVATION; N-OXIDES; HYDROGENATION; BENZAMIDES; ARYLATION;
D O I
10.1021/acs.orglett.6b02768
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel decahydropyrene synthesis has been successfully developed involving a tandem rhodium-catalyzed C-H activation/intramolecular Diels-Alder reaction/1,3-dipolar cycloaddition cascade process by using diazole as a traceless directing group. The advantage of this one-pot strategy is a quite simple, efficient, highly stereoselective, and unique product structure.
引用
收藏
页码:5524 / 5527
页数:4
相关论文
共 61 条
[1]   Entrapment of metallic palladium and a rhodium(I) complex in a silica sol-gel matrix - Formation of a highly active recyclable arene hydrogenation catalyst [J].
Abu-Reziq, R ;
Avnir, D ;
Miloslavski, I ;
Schumann, H ;
Blum, J .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 185 (1-2) :179-185
[2]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[3]   Multicatalysis: Advancing Synthetic Efficiency and Inspiring Discovery [J].
Ambrosini, Lisa M. ;
Lambert, Tristan H. .
CHEMCATCHEM, 2010, 2 (11) :1373-1380
[4]   Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].
Baudoin, Olivier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911
[5]   Liquid phase hydrogenation and hydrodenitrogenation of aromatic nitrogen-containing environmental pollutants [J].
Bovkun, Tatiana Tehila ;
Grayevsky, Michael ;
Sasson, Yoel ;
Blum, Jochanan .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 270 (1-2) :171-176
[6]   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
[7]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[8]   C-H Functionalization in organic synthesis [J].
Davies, Huw M. L. ;
Du Bois, Justin ;
Yu, Jin-Quan .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1855-1856
[9]   Weakly Coordinating Directing Groups for Ruthenium(II)-Catalyzed C-H Activation [J].
De Sarkar, Suman ;
Liu, Weiping ;
Kozhushkov, Sergei I. ;
Ackermann, Lutz .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) :1461-1479
[10]   Cooperative Tandem Catalysis by an Organometallic Complex and a Metalloenzyme [J].
Denard, Carl A. ;
Huang, Hua ;
Bartlett, Mark J. ;
Lu, Lu ;
Tan, Yichen ;
Zhao, Huimin ;
Hartwig, John F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (02) :465-469