Palladium-Catalyzed Dearomatization of Indoles with Alkynes: Construction of Spirocyclohexaneindolenines

被引:0
作者
Hu, Weiming [1 ]
Huang, Jiali [1 ]
Gao, Gang [2 ]
Guo, Wenting [1 ]
Yin, Fujun [3 ]
Sun, Yang [1 ]
Huang, Jingjiao [1 ]
Tao, Chuanzhou [1 ]
Tao, Li [4 ]
Hu, Huayou [5 ]
机构
[1] Jiangsu Ocean Univ, Sch Environm & Chem Engn, Jiangsu Key Lab Funct Control Technol Adv Mat, Lianyungang 222005, Jiangsu, Peoples R China
[2] Jiangsu Prov Lianyungang Flood Control & Motorized, Lianyungang 222000, Jiangsu, Peoples R China
[3] Jiangsu Ocean Univ, Jiangsu Inst Marine Resources Dev, Lianyungang 222005, Jiangsu, Peoples R China
[4] Jiangsu Ocean Univ, Off Acad Affairs, Lianyungang 222005, Jiangsu, Peoples R China
[5] Huaiyin Normal Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Chem Low Dimens Mat, Huaian 223300, Jiangsu, Peoples R China
关键词
ENANTIOSELECTIVE CONSTRUCTION; ALLYLIC DEAROMATIZATION; CASCADE REACTIONS; SILVER(I); ACCESS; YNONES; ACID;
D O I
10.1021/acs.joc.3c01041
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed dearomatization of indoles withalkynes hasbeen developed, providing an efficient route to access a variety ofsynthetically useful spirocyclohexaneindolenines in moderate to goodyields. The current method features a simple catalytic system, operationalsimplicity, and good functional group compatibility, which will contributesubstantially to the development of dearomatization to access spirocompounds. Besides, the ubiquitous existence of spiro molecules, includingspirocyclohexaneindolenines, in drugs and biological active moleculessuggests the potential application of this methodology in medicinalchemistry.
引用
收藏
页码:11335 / 11345
页数:11
相关论文
共 50 条
[41]   Palladium-catalyzed post-Ugi arylative dearomatization/Michael addition cascade towards plicamine analogues [J].
Liu, Chao ;
Zhao, Ruiqi ;
Song, Liangliang ;
Li, Zhenghua ;
Tian, Guilong ;
He, Yi ;
Van Meervelt, Luc ;
Peshkov, Vsevolod A. ;
Van der Eycken, Erik V. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (44) :9752-9757
[42]   Palladium-Catalyzed Regioselective C(4)-H Fluoroalkoxylation of Indoles Through Weak Chelation Assistance [J].
Vijaykumar, Muniyappa ;
Gonnade, Rajesh G. ;
Punji, Benudhar .
CHEMCATCHEM, 2025, 17 (02)
[43]   Palladium-Catalyzed Regioselective Oxidative Coupling of Indoles and One-Pot Synthesis of Acetoxylated Biindolyls [J].
Liang, Zuijun ;
Zhao, Jinlong ;
Zhang, Yuhong .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01) :170-177
[44]   Palladium-Catalyzed Dual Catalytic Synthesis of Heterocycles [J].
Ballav, Tamal ;
Chakrabortty, Rajesh ;
Das, Aniruddha ;
Ghosh, Suman ;
Ganesh, Venkataraman .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (30)
[45]   Palladium-Catalyzed Polymerization of Perfluoroalkyl Iodide and Aromatic Alkynes for the Synthesis of Perfluoroalkylated Poly(enyne)s [J].
Tian, Wen ;
Yao, Guanfei ;
Hu, Rongrong ;
Tang, Ben Zhong .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2023, 224 (01)
[46]   Palladium-Catalyzed Direct C-H Allylation of Electron-Deficient Polyfluoroarenes with Alkynes [J].
Zheng, Jun ;
Breit, Bernhard .
ORGANIC LETTERS, 2018, 20 (07) :1866-1870
[47]   Palladium-Catalyzed Trifluoroethylation of Terminal Alkynes with 1,1,1-Trifluoro-2-iodoethane [J].
Feng, Yi-Si ;
Xie, Chuan-Qi ;
Qiao, Wen-Long ;
Xu, Hua-Jian .
ORGANIC LETTERS, 2013, 15 (04) :936-939
[48]   Palladium-Catalyzed Double Decarboxylative [3+2] Annulation of Naphthalic Anhydrides with Internal Alkynes [J].
Kanganavaree, Chaipot ;
Kantarod, Kritchasorn ;
Worakul, Thanapat ;
Soorukram, Darunee ;
Kuhakarn, Chutima ;
Chakarawet, Khetpakorn ;
Wattanathana, Worawat ;
Surawatanawong, Panida ;
Reutrakul, Vichai ;
Leowanawat, Pawaret .
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (20) :15083-15090
[49]   Mechanism and Origin of Ligand-Controlled Chemo- and Regioselectivities in Palladium-Catalyzed Methoxycarbonylation of Alkynes [J].
Zhu, Ling ;
Liu, Ling-Jun ;
Jiang, Yuan-Ye ;
Liu, Peng ;
Fan, Xia ;
Zhang, Qi ;
Zhao, Yulei ;
Bi, Siwei .
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (11) :7136-7151
[50]   Spiroindoles as Intermediates/Products in Transition Metal-Catalyzed Dearomatization of Indoles [J].
Buttard, Floris ;
Guinchard, Xavier .
ACS CATALYSIS, 2023, 13 (14) :9442-9475