Hydride transfer enabled switchable dearomatization of indoles in the carbocyclic ring and the pyrrole ring

被引：46

作者：

Duan, Kang ^{[1
]}

Shi, Hongjin ^{[1
]}

Wang, Lin-Xuan ^{[1
]}

Li, Shuai-Shuai ^{[1
]}

Xu, Lubin ^{[1
]}

Xiao, Jian ^{[1
,2
]}

机构：

[1] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China

[2] Qingdao Agr Univ, Sch Marine Sci & Engn, Qingdao 266109, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 17期

关键词：

H BOND FUNCTIONALIZATION; MULTICOMPONENT CONDENSATION-REACTIONS; ORTHO-QUINONE METHIDES; C(SP(3))-H FUNCTIONALIZATION; ASYMMETRIC DEAROMATIZATION; TRANSFER/CYCLIZATION; CASCADE; CONSTRUCTION; TANDEM; AROMATIZATION;

D O I：

10.1039/d0qo00658k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydride transfer enabled the first success of the regioselective dearomatization of indoles in the carbocyclic ring and the pyrrole ring, which was induced byortho-quinone methides and vinylogous iminium intermediates. A variety of spiro cyclohexaketenes featuring the dearomatized indoles and carbazoles as well as spiroindolenines were provided in moderate to high yields. The formidable challenge of switchable dearomatization of fused bicyclic aromatic compounds was addressed.

引用

页码：2511 / 2517

页数：7

共 84 条

[1] Applications of ortho-Quinone Methides in the Synthesis of Natural Products [J].

Ai, Wenying ;

Liao, Daohong ;

Lei, Xiaoguang .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (08) :1615-1626

[2] Multicomponent Condensation Reactions via ortho-Quinone Methides [J].

Allen, Emily E. ;

Zhu, Calvin ;

Panek, James S. ;

Schaus, Scott E. .

ORGANIC LETTERS, 2017, 19 (07) :1878-1881

[3] Synthesis of Tetrahydro[1,3,4]triazepines via Redox-Neutral α-C(sp3)-H Amination of Cyclic Amines [J].

An, Xiao-De ;

Duan, Kang ;

Li, Xian-Jiang ;

Yang, Jian-Ming ;

Lu, Yong-Na ;

Liu, Qing ;

Xiao, Jian .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (18) :11839-11847

[4] Controllable Syntheses of Spiroindolenines and Benzazepinoindoles via Hexafluoroisopropanol-Mediated Redox-Neutral Cascade Process [J].

Bai, Guangxian ;

Dong, Fengying ;

Xu, Lubin ;

Liu, Yongjun ;

Wang, Liang ;

Li, Shuai-Shuai .

ORGANIC LETTERS, 2019, 21 (16) :6225-6230

[5] The Domestication of ortho-Quinone Methides [J].

Bai, Wen-Ju ;

David, Jonathan G. ;

Feng, Zhen-Gao ;

Weaver, Marisa G. ;

Wu, Kun-Liang ;

Pettus, Thomas R. R. .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (12) :3655-3664

[6] Catalytic Functionalization of Indoles in a New Dimension [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644

[7] Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols [J].

Barbato, Keith S. ;

Luan, Yi ;

Ramella, Daniele ;

Panek, James S. ;

Schaus, Scott E. .

ORGANIC LETTERS, 2015, 17 (23) :5812-5815

[8] Recent advances in spirocyclization of indole derivatives [J].

Bariwal, Jitender ;

Voskressensky, Leonid G. ;

Van der Eycken, Erik V. .

CHEMICAL SOCIETY REVIEWS, 2018, 47 (11) :3831-3848

[9] Chiral Phosphoric-Acid-Catalyzed Regioselective and Enantioselective C7-Friedel-Crafts Alkylation of 4-Aminoindoles with Trifluoromethyl Ketones [J].

Cai, Lu ;

Zhao, Yunlong ;

Huang, Tongkun ;

Meng, Shanshui ;

Jia, Xian ;

Chan, Albert S. C. ;

Zhao, Junling .

ORGANIC LETTERS, 2019, 21 (10) :3538-3542

[10] Rhodium(II)-Catalyzed Aryl C-H Carboxylation of 2-Pyridylphenols with CO2 [J].

Cai, Zhihua ;

Li, Shangda ;

Gao, Yuzhen ;

Li, Gang .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (20) :4005-4011

← 1 2 3 4 5 6 7 8 9 →