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

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 19期

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

页码：7702 / 7707

页数：6

共 81 条

[21] Structure-based design leads to the identification of lithium mimetics that block mania-like effects in rodents.: Possible new GSK-3β therapies for bipolar disorders [J].

Kozikowski, Alan P. ;

Gaisina, Irina N. ;

Yuan, Hongbin ;

Petukhov, Pavel A. ;

Blond, Sylvie Y. ;

Fedolak, Allison ;

Caldarone, Barbara ;

McGonigle, Paul .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (26) :8328-8332

[22] Electronic Nature of Ketone Directing Group as a Key To Control C-2 vs C-4 Alkenylation of Indoles [J].

Lanke, Veeranjaneyulu ;

Bettadapur, Kiran R. ;

Prabhu, Kandikere Ramaiah .

ORGANIC LETTERS, 2016, 18 (21) :5496-5499

[23] A synthesis of the welwistatin core [J].

Lauchli, Ryan ;

Shea, Kenneth J. .

ORGANIC LETTERS, 2006, 8 (23) :5287-5289

[24] Electrochemical Aminoxyl-Mediated α-Cyanation of Secondary Piperidines for Pharmaceutical Building Block Diversification [J].

Lennox, Alastair J. J. ;

Goes, Shannon L. ;

Webster, Matthew P. ;

Koolman, Hannes F. ;

Djuric, Stevan W. ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (36) :11227-11231

[25] Electrochemically Enabled, Nickel-Catalyzed Amination [J].

Li, Chao ;

Kawamata, Yu ;

Nakamura, Hugh ;

Vantourout, Julien C. ;

Liu, Zhiqing ;

Hou, Qinglong ;

Bao, Denghui ;

Starr, Jeremy T. ;

Chen, Jinshan ;

Yan, Ming ;

Baran, Phil S. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) :13088-13093

[26] Potassium iodide catalyzed simultaneous C3-formylation and N-aminomethylation of indoles with 4-substituted-N,N-dimethylanilines [J].

Li, Lan-Tao ;

Li, Hong-Ying ;

Xing, Li-Juan ;

Wen, Li-Juan ;

Wang, Peng ;

Wang, Bin .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (48) :9519-9522

[27] nBu4NI-catalyzed C3-formylation of indoles with N-methylaniline [J].

Li, Lan-Tao ;

Huang, Juan ;

Li, Hong-Ying ;

Wen, Li-Juan ;

Wang, Peng ;

Wang, Bin .

CHEMICAL COMMUNICATIONS, 2012, 48 (42) :5187-5189

[28] New Friedel-Crafts strategy for preparing 3-acylindoles [J].

Li, Lian-Hua ;

Niu, Zhi-Jie ;

Liang, Yong-Min .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (42) :7792-7796

[29] Aerobic Transition-Metal-Free Visible-Light Photoredox Indole C-3 Formylation Reaction [J].

Li, Xiang ;

Gu, Xiangyong ;

Li, Yongjuan ;

Li, Pixu .

ACS CATALYSIS, 2014, 4 (06) :1897-1900

[30] Recent Advances in the Electrochemical α-C-H Bond Functionalization of Carbonyl Compounds [J].

Liang, Sen ;

Xu, Kun ;

Zeng, Cheng-Chu ;

Tian, Hong-Yu ;

Sun, Bao-Guo .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (22) :4266-4292

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