N-Heterocyclic-Carbene-Catalyzed Synthesis of 2-Aryl Indoles

被引：77

作者：

Hovey, M. Todd ^{[1
]}

Check, Christopher T. ^{[1
]}

Sipher, Alexandra F. ^{[1
]}

Scheidt, Karl A. ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Ctr Mol Innovat & Drug Discovery, Evanston, IL 60208 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 36期

关键词：

asymmetric synthesis; cooperative effects; carbenes; O-QUINONE METHIDES; ACTIVATED DOUBLE-BONDS; ALPHA-ARYL KETONES; N-(ORTHO-CHLOROMETHYL)ARYL AMIDES; ENANTIOSELECTIVE SYNTHESIS; ACYLOIN CONDENSATIONS; INTERNAL ALKYNES; ENOL LACTONES; SULFUR YLIDES; NHC CATALYSIS;

D O I：

10.1002/anie.201405035

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent and efficient transition-metal-free catalytic synthesis of 2-aryl-indoles has been developed. The interception of a highly reactive and transient aza-ortho-quinone methide by an acyl anion equivalent generated through N-hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported.

引用

页码：9603 / 9607

页数：5

共 50 条

[31] Facile synthesis of 3-aryl benzofurans, 3-aryl benzothiophenes, 2-aryl indoles and their dimers
Umareddy, Pailla
Arava, Veera Reddy
SYNTHETIC COMMUNICATIONS, 2019, 49 (17) : 2156 - 2167
[32] N-Heterocyclic Carbene Catalyzed Stereoselective Synthesis of 2-Nitro-thiogalactosides
Hu, Yu-Long
Gou, Bo-Bo
Wang, Jiao
Zhao, Ming
Liu, Jia-Lin
Chen, Jie
Zhou, Ling
SYNTHESIS-STUTTGART, 2019, 51 (18): : 3451 - 3461
[33] N-Heterocyclic-Carbene-Catalyzed Regioselective Oxidative Ring-Opening of Epoxides with Aromatic Aldehydes: A Facile Entry to α-Acyloxyketones
Reddi, Rambabu N.
Gontala, Arjun
Prasad, Pragati K.
Sudalai, Arumugam
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (01) : 48 - 51
[34] N-Heterocyclic Carbene (NHC)/Ag(I) Co-catalyzed Synthesis of 2-Oxo-2-arylethyl Aryl Formates
Cheng, Li
Wang, Wenrong
Sun, Yuqian
Li, Tuanjie
Yu, Chenxia
Yao, Changsheng
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (04) : 1607 - 1613
[35] Oxidative N-Heterocyclic Carbene-Catalyzed Intramolecular Friedel-Crafts Alkylation of Indoles for the Synthesis of Spirocyclic Indolenines
Breuers, Christian B. J.
Daniliuc, Constantin G.
Studer, Armido
ORGANIC LETTERS, 2022, 24 (29) : 5314 - 5318
[36] N-Heterocyclic Carbene (NHC) Catalyzed Synthesis of α,α-Difluoro Esters
Dong, Xiuqin
Zhao, Yu-Ming
Sun, Jianwei
SYNLETT, 2013, 24 (10) : 1221 - 1224
[37] N-Heterocyclic Carbene-Catalyzed Synthesis of Pentafluorophenyl Sulfides
Xia Dengpeng
Luo Jinvun
He Lin
Cai Zhihua
Du Guangfen
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (02) : 622 - 630
[38] Recent Developments for the Synthesis of Heterocycles Catalyzed by N-Heterocyclic Carbene
Ding, Qiuping
Fan, Xiaona
Wu, Jie
CURRENT ORGANIC CHEMISTRY, 2014, 18 (06) : 700 - 718
[39] Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes
Zhang, Changhe
Lupton, David W.
ORGANIC LETTERS, 2017, 19 (17) : 4456 - 4459
[40] Enantioselective N-heterocyclic carbene-catalyzed synthesis of indenopyrones
Chen, Kun-Quan
Zhang, Han-Ming
Wang, Dong-Ling
Sun, De-Qun
Ye, Song
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (24) : 6694 - 6697

← 1 2 3 4 5 →