Carboxylative cyclization of propargylic amines with CO2 catalyzed by dendritic N-heterocyclic carbene-gold(I) complexes

被引:45
作者
Fujita, Ken-ichi [1 ]
Inoue, Kensuke [2 ]
Sato, Junichi [3 ]
Tsuchimoto, Teruhisa [2 ]
Yasuda, Hiroyuki [1 ,3 ]
机构
[1] Natl Inst Adv Ind Sci & Technol, Tsukuba Cent 5,1-1-1 Higashi, Tsukuba, Ibaraki 3058565, Japan
[2] Meiji Univ, Dept Appl Chem Sch Sci & Technol, Tama Ku, Kanagawa 2148571, Japan
[3] Ibaraki Univ, Grad Sch Sci & Engn, 2-1-1 Bunkyo, Ibaraki 3108512, Japan
关键词
NHC-gold(I) complex; Carbon dioxide; Propargylic amine; 2-Oxazolidinone; MIYAURA COUPLING REACTION; ARYL ETHER DENDRIMERS; CARBON-DIOXIDE; CHEMICAL-YIELD; AQUEOUS-MEDIA; DIELS-ALDER; OXAZOLIDINONES; LIGANDS; FIXATION; BEARING;
D O I
10.1016/j.tet.2016.01.016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We prepared several of a new type of dendritic N-heterocyclic carbene (NHC)-gold(I) complex. In particular, by employing an amphiphilic dendritic NHC-gold(I) complex having penta(ethylene glycol) units at the peripheral layer as a catalyst, the aqueous media carboxylative cyclization of propargylic amines proceeded smoothly to provide the corresponding 2-oxazolidinone at room temperature under atmospheric pressure of CO2. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1205 / 1212
页数:8
相关论文
共 44 条
[31]   Synthesis of novel dendritic 2,2′-bipyridine ligands and their application to lewis acid-catalyzed Diels-Alder and three-component condensation reactions [J].
Muraki, Takahito ;
Fujita, Ken-ichi ;
Kujime, Masato .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21) :7863-7870
[32]   Recent developments in carbon dioxide utilization for the production of organic chemicals [J].
Omae, Iwao .
COORDINATION CHEMISTRY REVIEWS, 2012, 256 (13-14) :1384-1405
[33]   Advancements in oxazolidinone synthesis utilizing carbon dioxide as a C1 source [J].
Pulla, Sharon ;
Felton, Charlette M. ;
Ramidi, Punnamchandar ;
Gartia, Yashraj ;
Ali, Nawab ;
Nasini, Udaya B. ;
Ghosh, Anindya .
JOURNAL OF CO2 UTILIZATION, 2013, 2 :49-57
[34]   Dendrimers in catalysis [J].
Reek, JNH ;
Arévalo, S ;
Van Heerbeek, R ;
Kamer, PCJ ;
Van Leeuwen, PWNM .
ADVANCES IN CATALYSIS, VOL 49, 2006, 49 :71-151
[35]   Recent developments in carbon dioxide utilization under mild conditions [J].
Riduan, Siti Nurhanna ;
Zhang, Yugen .
DALTON TRANSACTIONS, 2010, 39 (14) :3347-3357
[36]   Transformation of carbon dioxide [J].
Sakakura, Toshiyasu ;
Choi, Jun-Chul ;
Yasuda, Hiroyuki .
CHEMICAL REVIEWS, 2007, 107 (06) :2365-2387
[37]   Transition-metal-catalyzed reactions of propargylamine with carbon dioxide and carbon disulfide [J].
Shi, M ;
Shen, YM .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :16-21
[38]   Hexacationic Dendriphos Ligands in the Pd-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction: Scope and Mechanistic Studies [J].
Snelders, Dennis J. M. ;
van Koten, Gerard ;
Gebbink, Robertus J. M. Klein .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (32) :11407-11416
[39]   Aryl ether dendrimers with an interior metalloporphyrin functionality as a spectroscopic probe: Interpenetrating interaction with dendritic imidazoles [J].
Tomoyose, Y ;
Jiang, DL ;
Jin, RH ;
Aida, T ;
Yamashita, T ;
Horie, K ;
Yashima, E ;
Okamoto, Y .
MACROMOLECULES, 1996, 29 (15) :5236-5238
[40]   Catalysis inside dendrimers [J].
Twyman, LJ ;
King, ASH ;
Martin, IK .
CHEMICAL SOCIETY REVIEWS, 2002, 31 (02) :69-82