Recent Advances in the Catalytic Dearomatization of Naphthols

被引:89
作者
An, Juzeng [1 ]
Bandini, Marco [1 ,2 ]
机构
[1] Alma Mater Studiorum, Dipartimento Chim G Ciamician, Via Selmi 2, Bologna, Italy
[2] Consorzio CINMPIS, Via Selmi 2, Bologna, Italy
关键词
Asymmetric synthesis; Catalysis; Dearomatization; Naphthols; INTERMOLECULAR ARYLATIVE DEAROMATIZATION; ASYMMETRIC DEAROMATIZATION; BETA-NAPHTHOLS; OXIDATIVE DEAROMATIZATION; INTRAMOLECULAR DEAROMATIZATION; IRON CATALYSIS; GOLD CATALYSIS; 2-NAPHTHOLS; CONSTRUCTION; IRIDIUM;
D O I
10.1002/ejoc.202000107
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic dearomatization of naphthols offers a unique platform to rapidly access structurally complex and densely functionalized molecular architectures. Thermodynamically more favorable, with respect to the analogous phenol-variant, the transformation of the phenolic ring into the corresponding naphthalenone (cited here as naphthyl dearomatization) has faced a considerable amount of attention over the past decade with constant improvements towards stereocontrol. A collection of the most representative and recent catalytic variants involving carbon-carbon as well as carbon-heteroatom bond forming events are presented in thisMinireviewarticle.
引用
收藏
页码:4087 / 4097
页数:11
相关论文
共 97 条
[1]   PPh3AuTFA Catalyzed in the Dearomatization of 2-Naphthols with Allenamides [J].
An, Juzeng ;
Lombardi, Lorenzo ;
Grilli, Stefano ;
Bandini, Marco .
ORGANIC LETTERS, 2018, 20 (23) :7380-7383
[2]   Gold-Catalyzed Dearomatization of 2-Naphthols with Alkynes [J].
An, Juzeng ;
Parodi, Adriano ;
Monari, Magda ;
Castineira Reis, Marta ;
Silva Lopez, Carlos ;
Bandini, Marco .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (69) :17473-17477
[3]   Gold-catalyzed decorations of arenes and heteroarenes with C-C multiple bonds [J].
Bandini, Marco .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (03) :1358-1367
[4]   Recent advances in spirocyclization of indole derivatives [J].
Bariwal, Jitender ;
Voskressensky, Leonid G. ;
Van der Eycken, Erik V. .
CHEMICAL SOCIETY REVIEWS, 2018, 47 (11) :3831-3848
[5]   Iron Catalysis in Organic Synthesis [J].
Bauer, Ingmar ;
Knoelker, Hans-Joachim .
CHEMICAL REVIEWS, 2015, 115 (09) :3170-3387
[6]   Nucleophilic Dearomatization of Activated Pyridines [J].
Bertuzzi, Giulio ;
Bernardi, Luca ;
Fochi, Mariafrancesca .
CATALYSTS, 2018, 8 (12)
[7]   Dearomatizing benzene ring reductases [J].
Boll, M .
JOURNAL OF MOLECULAR MICROBIOLOGY AND BIOTECHNOLOGY, 2005, 10 (2-4) :132-142
[8]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[9]  
Cheng Q., 2016, ANGEW CHEM, V128, P3557
[10]   Chemo-, Diastereo-, and Enantioselective Iridium-Catalyzed Allylic Intramolecular Dearomatization Reaction of Naphthol Derivatives [J].
Cheng, Qiang ;
Wang, Ye ;
You, Shu-Li .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (10) :3496-3499