Synthesis of Functionalized Indoles via Palladium-Catalyzed Aerobic Oxidative Cycloisomerization of o-Allylanilines

被引:38
作者
Nallagonda, Rajender [1 ]
Rehan, Mohammad [1 ]
Ghorai, Prasanta [1 ]
机构
[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, India
关键词
ASSISTED INTRAMOLECULAR AMINATION; C BOND FORMATION; N-ARYL ENAMINES; MOLECULAR-OXYGEN; ALKALOIDS; ANILINES; ALKENES; CYCLIZATION; OLEFINS; AMINOPALLADATION;
D O I
10.1021/ol502244g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient strategy for the synthesis of 3-substituted 2-benzylindoles from stable and readily available o-allylanilines, prepared from anilines and allyl alcohols, has been developed. The reaction occurred via a regioselective 5-exo-trig intramolecular oxidative cycloisomerization using Pd(OAc)(2) as catalyst and molecular oxygen as an oxidant. The reaction showed a broad substrate scope with good to excellent yields.
引用
收藏
页码:4786 / 4789
页数:4
相关论文
共 50 条
[1]   Synthesis of Functionalized Indoles via Palladium-Catalyzed Aerobic Cycloisomerization of o-Allylanilines Using Organic Redox Cocatalyst [J].
Ning, Xiao-Shan ;
Wang, Mei-Mei ;
Qu, Jian-Ping ;
Kang, Yan-Biao .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21) :13523-13529
[2]   Palladium-catalyzed oxidative synthesis of SF5-indoles [J].
Chen, Jing ;
Xu, Lijin ;
Mi, Xueling .
TETRAHEDRON LETTERS, 2015, 56 (28) :4204-4206
[3]   Intramolecular Palladium-Catalyzed Oxidative Amination of Furans: Synthesis of Functionalized Indoles [J].
Makarov, Anton S. ;
Uchuskin, Maxim G. ;
Gevorgyan, Vladimir .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (22) :14010-14021
[4]   Synthesis of Functionalized Indoles via Palladium-Catalyzed Cyclization of N-(2-allylphenyl) Benzamide: A Method for Synthesis of Indomethacin Precursor [J].
Chang, Zhe ;
Ma, Tong ;
Zhang, Yu ;
Dong, Zheng ;
Zhao, Heng ;
Zhao, Depeng .
MOLECULES, 2020, 25 (05)
[5]   Palladium-Catalyzed Cycloisomerization and Aerobic Oxidative Cycloisomerization of Homoallenyl Amides: A Facile and Divergent Approach to 2-Aminofurans [J].
Cheng, Cungui ;
Liu, Shuiyou ;
Zhu, Gangguo .
ORGANIC LETTERS, 2015, 17 (06) :1581-1584
[6]   Palladium-catalyzed synthesis of indoles via intramolecular Heck reaction [J].
Yang, Hailong ;
Sun, Peng ;
Zhu, Yan ;
Yan, Hong ;
Lu, Linhua ;
Liu, Defu ;
Rong, Guangwei ;
Mao, Jincheng .
CATALYSIS COMMUNICATIONS, 2013, 38 :21-25
[7]   Effective synthesis of bicyclodienes via palladium-catalyzed asymmetric allylic alkylation and ruthenium-catalyzed cycloisomerization [J].
Havare, Nizam .
TURKISH JOURNAL OF CHEMISTRY, 2020, 44 (06) :1445-+
[8]   Synthesis of Tetracyclic Flavonoids via Palladium-Catalyzed Intramolecular Oxidative Cyclization [J].
Ayyagari, Narasimham ;
Belani, Jitendra D. .
SYNLETT, 2014, 25 (16) :2350-2354
[9]   Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C-H activation [J].
Rago, Alexander J. ;
Dong, Guangbin .
GREEN SYNTHESIS AND CATALYSIS, 2021, 2 (02) :216-227
[10]   Regioselective palladium-catalyzed olefination of coumarins via aerobic oxidative Heck reactions [J].
Min, Minsik ;
Kim, Yechan ;
Hong, Sungwoo .
CHEMICAL COMMUNICATIONS, 2013, 49 (02) :196-198