Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes

被引:25
作者
Yang, Liquan [1 ]
Liu, Zhaoran [1 ]
Li, Yujun [1 ]
Lei, Ning [1 ]
Shen, Yanling [1 ]
Zheng, Ke [1 ]
机构
[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H BOND; PALLADIUM-CATALYZED CARBONYLATION; FORMAL TOTAL-SYNTHESIS; TERTIARY-AMINES; ANODIC-OXIDATION; ELECTROORGANIC CHEMISTRY; EFFICIENT ROUTE; METAL-FREE; FORMYLATION; CLEAVAGE;
D O I
10.1021/acs.orglett.9b02433
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reported herein is an effective strategy for oxidative cross-coupling of indoles with various aldehydes. The strategy is based on a two-step transformation via a well-known Mannich-type reaction and a C-N bond cleavage for carbonyl introduction. The key step-the C-N bond cleavage of the Mannich product-was enabled by electrochemistry. This strategy (with over 40 examples) ensures excellent functional-group tolerance as well as late-stage functionalization of pharmaceutical molecules.
引用
收藏
页码:7702 / 7707
页数:6
相关论文
共 81 条
[11]   Iridium-and Rhodium-Catalyzed Directed C-H Heteroarylation of Benzaldehydes with Benziodoxolone Hypervalent Iodine Reagents [J].
Grenet, Erwann ;
Waser, Jerome .
ORGANIC LETTERS, 2018, 20 (05) :1473-1476
[12]   Palladium-Catalyzed Carbonylation of Indoles using Aryl Formates as Bifunctional Reagents: A Route to Indol-3-yl Aryl Ketones [J].
Gu, Li-Jun ;
Wang, Yu-Shen ;
Zhang, Hong-Tao ;
Tang, Huai-Jun ;
Li, Gan-Peng ;
Yuan, Ming-Long .
CHEMCATCHEM, 2016, 8 (13) :2206-2209
[13]   Acylation of indoles via photoredox catalysis: a route to 3-acylindoles [J].
Gu, Lijun ;
Jin, Cheng ;
Liu, Jiyan ;
Zhang, Hongtao ;
Yuan, Minglong ;
Li, Ganpeng .
GREEN CHEMISTRY, 2016, 18 (05) :1201-1205
[14]   Metal-free, visible-light-mediated transformation of aryl diazonium salts and (hetero)arenes: an efficient route to aryl ketones [J].
Gu, Lijun ;
Jin, Cheng ;
Liu, Jiyan .
GREEN CHEMISTRY, 2015, 17 (07) :3733-3736
[15]   ANODIC-OXIDATION PATHWAYS OF N-ALKYLANILINES [J].
HAND, RL ;
NELSON, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (03) :850-860
[16]   Bronsted Acid Catalyzed Nitrile Synthesis from Aldehydes Using Oximes via Transoximation at Ambient Temperature [J].
Hyodo, Kengo ;
Togashi, Kosuke ;
Oishi, Naoki ;
Hasegawa, Genna ;
Uchida, Kingo .
ORGANIC LETTERS, 2017, 19 (11) :3005-3008
[17]   Synthesis of 3-Acylindoles by Palladium-Catalyzed Acylation of Free (N-H) Indoles with Nitriles [J].
Jiang, Tao-Shan ;
Wang, Guan-Wu .
ORGANIC LETTERS, 2013, 15 (04) :788-791
[18]   Use of Electrochemistry in the Synthesis of Heterocyclic Structures [J].
Jiang, Yangye ;
Xu, Kun ;
Zeng, Chengchu .
CHEMICAL REVIEWS, 2018, 118 (09) :4485-4540
[19]   Electrochemical strategies for C-H functionalization and C-N bond formation [J].
Karkas, Markus D. .
CHEMICAL SOCIETY REVIEWS, 2018, 47 (15) :5786-5865
[20]   Palladium-catalyzed oxidative C-H bond coupling of indoles and benzaldehydes: a new approach to the synthesis of 3-benzoylindoles [J].
Kianmehr, Ebrahim ;
Kazemi, Shahrzad ;
Foroumadi, Alireza .
TETRAHEDRON, 2014, 70 (02) :349-354