Ru(II)-Catalyzed Regioselective C-H Alkenylation of Indoles Using Cyanomethyl Directing Group

被引：1
作者：
Yan Fachao [1 ,2 ]
Li Yang [1 ,2 ]
Li Yudong [1 ]
Makha, Mohamed [1 ]
Li Yuehui [1 ]
机构：
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys LICP, Suzhou Res Inst LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 42卷 / 07期
基金：
中国国家自然科学基金;
关键词：
Ru(II)-catalysis; C(2)-alkenylation; indole; cyanomethyl directing group; C-H bond functionalization; CATALYTIC FUNCTIONALIZATION; TETRASUBSTITUTED ALKENES; BOND FORMATION; OLEFINATION; ACTIVATION; ARENES; PYRROLES; ALKYNES; C2-ALKENYLATION; HYDROARYLATION;
D O I：
10.6023/cjoc202203017
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A ruthenium-catalyzed C(2)-alkenylation of indole derivatives by employing cyanomethyl as the directing group was developed for the first time. Site-selective alkenylation was achieved for a broad scope of alkenes as coupling partners with a large number of indoles bearing synthetically useful functional groups. The protocol represents a novel method for C(2)-alkenylation of indoles affording biologically relevant indolic compounds. The reaction conditions were mild and it showed good substrate scope and functional group compatibility. Ester group, cyano group, iodine, bromine, fluorine and trifluoromethyl were all well compatible. The directing group can be easily removed under relatively mild conditions to form N-H indoles.
引用
收藏
页码：2192 / 2200
页数：9
相关论文
共 85 条
[1]   Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations [J].
Ackermann, Lutz .
SYNLETT, 2007, (04) :507-526
[2]   Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles [J].
Anbarasan, Pazhamalai ;
Schareina, Thomas ;
Beller, Matthias .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5049-5067
[3]   Remote para-C-H Functionalization of Arenes by a D-Shaped Biphenyl Template-Based Assembly [J].
Bag, Sukdev ;
Patra, Tuhin ;
Modak, Atanu ;
Deb, Arghya ;
Maity, Soham ;
Dutta, Uttam ;
Dey, Aniruddha ;
Kancherla, Rajesh ;
Maji, Arun ;
Hazra, Avijit ;
Bera, Milan ;
Maiti, Debabrata .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (37) :11888-11891
[4]   ` Intramolecular Gold-Catalyzed and NaH-Supported Cyclization Reactions of N-Propargyl Indole Derivatives with Pyrazole and Pyrrole Rings: Synthesis of Pyrazolodiazepinoindole, Pyrazolopyrazinoindole, and Pyrrolopyrazinoindole [J].
Basceken, Sinan ;
Kaya, Serdal ;
Balci, Metin .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) :12552-12561
[5]   C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Sottocornola, Silvia .
CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365
[6]   Palladium(II)-Catalyzed meta-C-H Olefination: Constructing Multisubstituted Arenes through Homo-Diolefination and Sequential Hetero-Diolefination [J].
Bera, Milan ;
Maji, Arun ;
Sahoo, Santosh K. ;
Maiti, Debabrata .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (29) :8515-8519
[7]   Meta-Selective Arene C-H Bond Olefination of Arylacetic Acid Using a Nitrile-Based Directing Group [J].
Bera, Milan ;
Modak, Atanu ;
Patra, Tuhin ;
Maji, Arun ;
Maiti, Debabrata .
ORGANIC LETTERS, 2014, 16 (21) :5760-5763
[8]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
[9]   Manganese-catalyzed synthesis of monofluoroalkenes via C-H activation and C-F cleavage [J].
Cai, Sai-Hu ;
Ye, Lu ;
Wang, Ding-Xing ;
Wang, Yi-Qiu ;
Lai, Lin-Jie ;
Zhu, Chuan ;
Feng, Chao ;
Loh, Teck-Peng .
CHEMICAL COMMUNICATIONS, 2017, 53 (62) :8731-8734
[10]   Recent Advances in the Catalytic Functionalization of "Electrophilic" Indoles [J].
Cerveri, Alessandro ;
Bandini, Marco .
CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (03) :287-294
123456789