B(C6F5)3-catalyzed Markovnikov addition of indoles to aryl alkynes: an approach toward bis(indolyl)alkanes

被引:34
作者
Ling, Fei [1 ]
Xiao, Lian [1 ]
Fang, Lu [1 ]
Feng, Cong [1 ]
Xie, Zhen [1 ]
Lv, Yaping [1 ]
Zhong, Weihui [1 ]
机构
[1] Zhejiang Univ Technol, Minist Educ, Coll Pharmaceut Sci, Key Lab Green Pharmaceut Technol & Related Equipm, Hangzhou 310014, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
FRUSTRATED LEWIS PAIR; H BOND; CARBONYL-COMPOUNDS; TERMINAL ALKYNES; BIS(INDOLYL)METHANE; HYDROAMINATION; HYDROGENATIONS; HETEROARENES; ACTIVATION; EFFICIENT;
D O I
10.1039/c8ob02805b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first example of the metal- and solvent-free B(C6F5)(3)-catalyzed Markovnikov addition of indoles to aryl alkynes was disclosed. Both N-H and N-protected indoles were tolerated, leading to a wide spectrum of versatile bis(indolyl)alkanes in moderate to good yields with high regioselectivities.
引用
收藏
页码:9274 / 9278
页数:5
相关论文
共 58 条
[1]   B(C6F5)3-catalyzed hydrosilation of imines via silyliminium intermediates [J].
Blackwell, JM ;
Sonmor, ER ;
Scoccitti, T ;
Piers, WE .
ORGANIC LETTERS, 2000, 2 (24) :3921-3923
[2]   Alkenylation of Arenes and Heteroarenes with Alkynes [J].
Boyarskiy, Vadim P. ;
Ryabukhin, Dmitry S. ;
Bokach, Nadezhda A. ;
Vasilyev, Aleksander V. .
CHEMICAL REVIEWS, 2016, 116 (10) :5894-5986
[3]   C-H bond functionalization of aromatic heterocycles with chelating dicarbene palladium(II) and platinum(II) complexes [J].
Buscemi, Gabriella ;
Biffis, Andrea ;
Tubaro, Cristina ;
Basato, Marino ;
Graiff, Claudia ;
Tiripicchio, Antonio .
APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (04) :285-290
[4]   Dry reaction of indoles with carbonyl compounds on montmorillonite K10 clay: a mild, expedient synthesis of diindolylalkanes and vibrindole A [J].
Chakrabarty, M ;
Ghosh, N ;
Basak, R ;
Harigaya, Y .
TETRAHEDRON LETTERS, 2002, 43 (22) :4075-4078
[5]   B(C6F5)3-Catalyzed Transfer Hydrogenation of Imines and Related Heteroarenes Using Cyclohexa-1,4-dienes as a Dihydrogen Source [J].
Chatterjee, Indranil ;
Oestreich, Martin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (06) :1965-1968
[6]   Dibenzopentalenes from B(C6F5)3-Induced Cyclization Reactions of 1,2-Bis(phenylethynyl)benzenes [J].
Chen, Chao ;
Harhausen, Marcel ;
Liedtke, Rene ;
Bussmann, Kathrin ;
Fukazawa, Aiko ;
Yamaguchi, Shigehiro ;
Petersen, Jeffrey L. ;
Daniliuc, Constantin G. ;
Froehlich, Roland ;
Kehr, Gerald ;
Erker, Gerhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (23) :5992-5996
[7]   Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones [J].
Chen, DP ;
Yu, LB ;
Wang, PG .
TETRAHEDRON LETTERS, 1996, 37 (26) :4467-4470
[8]   Chemicals from Alkynes with Palladium Catalysts [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2014, 114 (03) :1783-1826
[9]   Regioselective synthesis and biological evaluation of bis(indolyl)methane derivatized 1,4-disubstituted 1,2,3-bistriazoles as anti-infective agents [J].
Damodiran, M. ;
Muralidharan, D. ;
Perumal, Paramasivan T. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (13) :3611-3614
[10]   B(C6F5)3-Promoted hydrogenations of N-heterocycles with ammonia borane [J].
Ding, Fangwei ;
Zhang, Yiliang ;
Zhao, Rong ;
Jiang, Yanqiu ;
Bao, Robert Li-Yuan ;
Lin, Kaifeng ;
Shi, Lei .
CHEMICAL COMMUNICATIONS, 2017, 53 (66) :9262-9264