Palladium-Catalyzed Dearomatization of Indoles with Alkynes: Construction of Spirocyclohexaneindolenines

被引：0

作者：

Hu, Weiming ^{[1
]}

Huang, Jiali ^{[1
]}

Gao, Gang ^{[2
]}

Guo, Wenting ^{[1
]}

Yin, Fujun ^{[3
]}

Sun, Yang ^{[1
]}

Huang, Jingjiao ^{[1
]}

Tao, Chuanzhou ^{[1
]}

Tao, Li ^{[4
]}

Hu, Huayou ^{[5
]}

机构：

[1] Jiangsu Ocean Univ, Sch Environm & Chem Engn, Jiangsu Key Lab Funct Control Technol Adv Mat, Lianyungang 222005, Jiangsu, Peoples R China

[2] Jiangsu Prov Lianyungang Flood Control & Motorized, Lianyungang 222000, Jiangsu, Peoples R China

[3] Jiangsu Ocean Univ, Jiangsu Inst Marine Resources Dev, Lianyungang 222005, Jiangsu, Peoples R China

[4] Jiangsu Ocean Univ, Off Acad Affairs, Lianyungang 222005, Jiangsu, Peoples R China

[5] Huaiyin Normal Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Chem Low Dimens Mat, Huaian 223300, Jiangsu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 15期

关键词：

ENANTIOSELECTIVE CONSTRUCTION; ALLYLIC DEAROMATIZATION; CASCADE REACTIONS; SILVER(I); ACCESS; YNONES; ACID;

D O I：

10.1021/acs.joc.3c01041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed dearomatization of indoles withalkynes hasbeen developed, providing an efficient route to access a variety ofsynthetically useful spirocyclohexaneindolenines in moderate to goodyields. The current method features a simple catalytic system, operationalsimplicity, and good functional group compatibility, which will contributesubstantially to the development of dearomatization to access spirocompounds. Besides, the ubiquitous existence of spiro molecules, includingspirocyclohexaneindolenines, in drugs and biological active moleculessuggests the potential application of this methodology in medicinalchemistry.

引用

页码：11335 / 11345

页数：11

共 50 条

[41] Palladium-Catalyzed Direct Arylation of Indoles with Cyclohexanones
Chen, Shanping
Liao, Yunfeng
Zhao, Feng
Qi, Hongrui
Liu, Saiwen
Deng, Guo-Jun
ORGANIC LETTERS, 2014, 16 (06) : 1618 - 1621
[42] Palladium-Catalyzed Oxidative Amination of α-Olefins with Indoles
Bhatt, Shreeja
Wang, Ya-Nong
Pham, Hoang T. P.
Hull, Kami L.
ORGANIC LETTERS, 2022, 24 (31) : 5746 - 5750
[43] Palladium-catalyzed cyclization/carboalkoxylation of alkenyl indoles
Liu, C
Widenhoefer, RA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) : 10250 - 10251
[44] Palladium-Catalyzed Dearomatizing Difunctionalization of Indoles and Benzofurans
Ramella, Vincenzo
He, Zhiheng
Daniliuc, Constantin G.
Studer, Armido
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (13) : 2268 - 2273
[45] Palladium-catalyzed asymmetric decarboxylative benzylation of alkynes
Mendis, Shehani N.
Tunge, Jon A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
[46] Palladium-Catalyzed Stereospecific Decarboxylative Benzylation of Alkynes
Mendis, Shehani N.
Tunge, Jon A.
ORGANIC LETTERS, 2015, 17 (21) : 5164 - 5167
[47] Synthesis of β- and γ-carbolines by the palladium-catalyzed iminoannulation of alkynes
Zhang, HM
Larock, RC
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26): : 9318 - 9330
[48] Palladium-Catalyzed Intermolecular Aryliodination of Internal Alkynes
Lee, Yong Ho
Morandi, Bill
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (19) : 6444 - 6448
[49] PALLADIUM-CATALYZED CYCLOADDITION OF ALKYNES (RCCR') WITH DIMETHYLGERMYLENE
BRAUER, H
NEUMANN, WP
SYNLETT, 1991, (06) : 431 - 432
[50] Palladium-Catalyzed Regioselective Difluoroalkylation and Carbonylation of Alkynes
Wang, Qang
He, Yu-Tao
Zhao, Jia-Hui
Qiu, Yi-Feng
Zheng, Lan
Hu, Jing-Yuan
Yang, Yu-Chen
Liu, Xue-Yuan
Liang, Yong-Min
ORGANIC LETTERS, 2016, 18 (11) : 2664 - 2667

← 1 2 3 4 5 →