Carbocyclisation of alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals

被引:266
作者
Abu Sohel, Shariar Md. [1 ]
Liu, Rai-Shung [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
关键词
CONTAINING CARBONYL YLIDES; HYDRATIVE CYCLIZATION; 4+2 CYCLOADDITION; C-C; CYCLOISOMERIZATIONS; CARBOCYCLIZATION; GENERATION; HYDROXYCYCLIZATION; ALKOXYCYCLIZATION; CONSTRUCTION;
D O I
10.1039/b807499m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This tutorial review covers recent developments in catalytic carbocyclisation of functionalised alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals. Substrates of such reactions require a tethered functionality to react with the alkyne to complete a carbocyclic ring. We classify the reactions according to the tethered functionalities to illustrate the diversity of the carbocyclisations; these substrates include: (1) alkyne-alkyne, (2) alkyne-allene, (3) alkyne-alkene, (4) oxo-alkynes and (5) oxo-diynes and triynes. Besides their mechanistic interest, these reactions meet atom economy criteria because complex and functionalised carbocyclic products are easily assembled in a cascade sequence from readily available alkynes and nucleophiles.
引用
收藏
页码:2269 / 2281
页数:13
相关论文
共 48 条
[1]   Gold(I)-catalysed arylation of 1,6-enynes: different site reactivity of cyclopropyl gold carbenes [J].
Amijs, Catelijne H. M. ;
Ferrer, Catalina ;
Echavarren, Antonio M. .
CHEMICAL COMMUNICATIONS, 2007, (07) :698-700
[2]   AuBr3-catalyzed [4+2] benzannulation between an enynal unit and enol [J].
Asao, N ;
Aikawa, H ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7458-7459
[3]   Functionalized 1,2-dihydronaphthalenes from the Cu(OTf)2-catalyzed [4+2] cycloaddition of o-alkynyl(oxo)benzenes with alkenes [J].
Asao, N ;
Kasahara, T ;
Yamamoto, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) :3504-3506
[4]   PtII-catalyzed synthesis of 9-oxabicyclo-[3.3.1]nona-2,6-dienes from 2-alkynyl-1-carbonylbenzenes and allylsilanes by an allylation/annulation cascade [J].
Bhunia, Sabyasachi ;
Wang, Kuo-Chang ;
Liu, Rai-Shung .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) :5063-5066
[5]   Gold(I)-catalyzed 5-endo hydroxy- and alkoxycyclization of 1,5-enynes:: Efficient access to functionalized cyclopentenes [J].
Buzas, Andrea K. ;
Istrate, Florin M. ;
Gagosz, Fabien .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1141-1144
[6]   PtCl2-catalyzed cycloisomerizations of allenynes [J].
Cadran, N ;
Cariou, K ;
Hervé, G ;
Aubert, C ;
Fensterbank, L ;
Malacria, M ;
Marco-Contelles, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3408-3409
[7]   Diversity in platinum-catalyzed hydrative cyclization of trialkyne substrates to form tetracyclic ketones [J].
Chang, Hsu-Kai ;
Liao, Yen-Chen ;
Liu, Rai-Shung .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21) :8139-8141
[8]   PtCl2-catalyzed hydrative cyclization of trialkyne functionalities to form bicyclic spiro ketones [J].
Chang, Hsu-Kai ;
Datta, Swarup ;
Das, Arindam ;
Odedra, Arjan ;
Liu, Rai-Shung .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) :4744-4747
[9]   Ruthenium-catalyzed hydrative cyclization of 1,5-enynes [J].
Chen, YY ;
Ho, DM ;
Lee, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) :12184-12185
[10]   Platinum- and gold-catalyzed hydrative carbocyclization of oxo diynes for one-pot synthesis of benzopyrones and bicyclic spiro ketones [J].
Das, Arindam ;
Chang, Hsu-Kai ;
Yang, Cheng-Hua ;
Liu, Rai-Shung .
ORGANIC LETTERS, 2008, 10 (18) :4061-4064