Gold-catalyzed synthesis of 1,3-disubstituted benzenes through tandem allylation/cyclization reaction of alkynals

被引:17
作者
Bhunia, Sabyasachi [1 ]
Abu Sohel, Shariar Md. [1 ]
Yang, Chao-Chin [1 ]
Lush, Shie-Fu [2 ]
Shen, Fwu-Ming [3 ]
Liu, Rai-Shung [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
[2] Yuan Pei Univ, Dept Biotechnol, Hsinchu, Taiwan
[3] Yuan Pei Univ, Dept Med Lab Sci & Biotechnol, Hsinchu, Taiwan
关键词
Allylation; Alkynal; Benzenes; Catalysis; Tandem reaction; CYCLOISOMERIZATION REACTIONS; SKELETAL REORGANIZATION; PLATINUM; ENYNES; CYCLIZATION; 1,5-ENYNES; BENZANNULATION; ACCESS; REARRANGEMENTS; ISOMERIZATION;
D O I
10.1016/j.jorganchem.2008.10.049
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Treatment of alkynals with 2-substituted allylsilanes and PPh3AuCl/AgOTf (5/3 mol%) catalyst led to formation of 1,3-disubstituted benzenes efficiently. This reaction sequence comprises an initial allylation of aldehyde, followed by cycloisomerization of enynes; PPh3AuOTf is active in both steps. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:566 / 570
页数:5
相关论文
共 71 条
[1]  
[Anonymous], 2001, NEW CHEM
[2]  
[Anonymous], 2000, STIMULATING CONCEPTS
[3]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[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]   PtCl2-catalyzed transannular cycloisomerization of 1,5-enynes:: A new efficient regio- and stereocontrolled access to tricyclic derivatives [J].
Blaszykowski, C ;
Harrak, Y ;
Gonçalves, MH ;
Cloarec, JM ;
Dhimane, AL ;
Fensterbank, L ;
Malacria, M .
ORGANIC LETTERS, 2004, 6 (21) :3771-3774
[6]   Golden opportunities in stereoselective catalysis [J].
Bongers, Nadine ;
Krause, Norbert .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2178-2181
[7]   Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones [J].
Buzas, Andrea ;
Gagosz, Fabien .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12614-12615
[8]   Skeletal reorganization of enynes to 1-vinylcycloalkenes catalyzed by GaCl3 [J].
Chatani, N ;
Inoue, H ;
Kotsuma, T ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) :10294-10295
[9]   Construction of novel polycyclic ring systems by transition-metal-catalyzed cycloisomerization of ene-ene-ynes. Interception of a carbenoid intermediate in skeletal reorganization of enynes [J].
Chatani, N ;
Kataoka, K ;
Murai, S ;
Furukawa, N ;
Seki, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :9104-9105
[10]   PtCl2-catalyzed conversion of 1,6- and 1,7-enynes to 1-vinylcycloalkenes. Anomalous bond connection in skeletal reorganization of enynes [J].
Chatani, N ;
Furukawa, N ;
Sakurai, H ;
Murai, S .
ORGANOMETALLICS, 1996, 15 (03) :901-903