Palladium-catalyzed tandem addition/cyclization in aqueous medium: synthesis of 2-arylindoles

被引：17

作者：

Yu, Shuling ^{[1
]}

Hu, Kun ^{[1
]}

Gong, Julin ^{[1
]}

Qi, Linjun ^{[1
]}

Zhu, Jianghe ^{[1
]}

Zhang, Yetong ^{[1
]}

Cheng, Tianxing ^{[1
]}

Chen, Jiuxi ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 20期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; C-H ACTIVATION; DIRECT C-2 ARYLATION; ARYLBORONIC ACIDS; ARYL KETONES; ROOM-TEMPERATURE; REGIOSELECTIVE SYNTHESIS; REDUCTIVE CYCLIZATION; 2-SUBSTITUTED INDOLES; ORGANIC-REACTIONS;

D O I：

10.1039/c7ob00572e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient protocol to construct 2-arylindoles was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover, the utility of this catalytic tandem transformation was also demonstrated in an efficient gram-scale synthesis. This method provides an alternative synthetic tool for accessing a more diverse array of 2-arylindoles.

引用

页码：4300 / 4307

页数：8

共 97 条

[61] Nitrile Ligated Transition Metal Complexes with Weakly Coordinating Counteranions and Their Catalytic Applications [J].

Rach, Silvana F. ;

Kuehn, Fritz E. .

CHEMICAL REVIEWS, 2009, 109 (05) :2061-2080

[62]

Rappoport Z., 1970, CHEM CYANO GROUP

[63] 3-(4-fluoropiperidin-3-yl)-2-phenylindoles as high affinity, selective, and orally bioavailable h5-HT2A receptor antagonist [J].

Rowley, M ;

Hallett, DJ ;

Goodacre, S ;

Moyes, C ;

Crawforth, J ;

Sparey, TJ ;

Patel, S ;

Marwood, R ;

Patel, S ;

Thomas, S ;

Hitzel, L ;

O'Connor, D ;

Szeto, N ;

Castro, JL ;

Hutson, PH ;

MacLeod, AM .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (10) :1603-1614

[64] Copper-Catalyzed Activation of Dioxygen: Oxidative Cyclization of 2-Arylindoles [J].

Sang, Peng ;

Xie, Yongju ;

Zou, Jianwei ;

Zhang, Yuhong .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (10) :1873-1878

[65]

Schneider M. R., 1986, DRUGS FUTURE, V11, P1023

[66] RETRACTED: Selective C-arylation of free (NH)-heteroarenes via catalytic C-H bond functionalization (Retracted Article. See vol 128, pg 8364, 2006) [J].

Sezen, B ;

Sames, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (18) :5274-5275

[67] Dirhodium(II)-catalyzed intramolecular C-H amination of aryl azides [J].

Shen, Meihua ;

Leslie, Brooke E. ;

Driver, Tom G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) :5056-5059

[68] Copper-catalyzed direct C-H arylation of pyridine N-oxides with arylboronic esters: one-pot synthesis of 2-arylpyridines [J].

Shen, Yan ;

Chen, Jiuxi ;

Liu, Miaochang ;

Ding, Jinchang ;

Gao, Wenxia ;

Huang, Xiaobo ;

Wu, Huayue .

CHEMICAL COMMUNICATIONS, 2014, 50 (33) :4292-4295

[69] Microwave Heated Continuous Flow Palladium(II)-Catalyzed Desulfitative Synthesis of Aryl Ketones [J].

Skillinghaug, Bobo ;

Rydfjord, Jonas ;

Savmarker, Jonas ;

Larhed, Mats .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (11) :2005-2011

[70] Palladium(II)-Catalyzed Desulfitative Synthesis of Aryl Ketones from Sodium Arylsulfinates and Nitriles: Scope, Limitations, and Mechanistic Studies [J].

Skillinghaug, Bobo ;

Skold, Christian ;

Rydfjord, Jonas ;

Svensson, Fredrik ;

Behrends, Malte ;

Savmarker, Jonas ;

Sjoberg, Per J. R. ;

Larhed, Mats .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (24) :12018-12032

← 1 2 3 4 5 6 7 8 9 10 →