Gold-catalyzed intramolecular [3+2]-cycloaddition of arenyne-yne functionalities

被引:120
作者
Lian, Jian-Jou [1 ]
Chen, Po-Chiang [1 ]
Lin, Yau-Ping [1 ]
Ting, Hao-Chun [1 ]
Liu, Rai-Shung [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
关键词
D O I
10.1021/ja0643826
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a new efficient intramolecular [3 + 2]-cycloaddition of unactivated arenyne (or enyne)-yne functionalities, catalyzed mainly by the AuPPh3SbF6 complex (2 mol %) under ambient conditions. The value of this cyclization is reflected by its applicability to a wide range of diyne substrates bearing various functional groups. Copyright © 2006 American Chemical Society.
引用
收藏
页码:11372 / 11373
页数:2
相关论文
共 19 条
[1]  
BADRIEH Y, 1990, J MOL CATAL, V60, P323
[2]   Strained cyclic cumulene intermediates in Diels-Alder cycloadditions of enynes and diynes [J].
Burrell, RC ;
Daoust, KJ ;
Bradley, AZ ;
DiRico, KJ ;
Johnson, RP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (17) :4218-4219
[3]   Synthesis of highly substituted indolines and indoles via intramolecular [4+2] cycloaddition of ynamides and conjugated enynes [J].
Dunetz, JR ;
Danheiser, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5776-5777
[4]   Steric hindrance facilitated synthesis of enynes and their intramolecular [4+2] cycloaddition with alkynes [J].
González, JJ ;
Francesch, A ;
Cárdenas, DJ ;
Echavarren, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2854-2857
[5]   Intramolecular [4+2] cycloadditions of benzynes with conjugated enynes, arenynes, and dienes [J].
Hayes, ME ;
Shinokubo, H ;
Danheiser, RL .
ORGANIC LETTERS, 2005, 7 (18) :3917-3920
[6]   Gold(I)-catalyzed stereoselective olefin cyclopropanation [J].
Johansson, MJ ;
Gorin, DJ ;
Staben, ST ;
Toste, FD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18002-18003
[7]   Gold(I)-catalyzed conia-ene reaction of β-ketoesters with alkynes [J].
Kennedy-Smith, JJ ;
Staben, ST ;
Toste, FD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) :4526-4527
[8]   Ligand effects in gold- and platinum-catalyzed cyclization of enynes:: Chiral gold complexes for enantioselective alkoxycyclization [J].
Muñoz, MP ;
Adrio, J ;
Carretero, JC ;
Echavarren, AM .
ORGANOMETALLICS, 2005, 24 (06) :1293-1300
[9]   Intramolecular [4+2] cycloadditions of 1,3-enynes or arylalkynes with alkenes with highly reactive cationic phosphine Au(I) complexes [J].
Nieto-Oberhuber, C ;
López, S ;
Echavarren, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6178-6179
[10]   Intramolecular dehydro Diels-Alder reactions of diarylacetylenes:: Switching between benzo[b]- and benzo[c]fluorenones as products by controlling the rearrangement of cyclic allene intermediates [J].
Rodríguez, D ;
Martínez-Esperón, MF ;
Navarro-Vázquez, A ;
Castedo, L ;
Domínguez, D ;
Saá, C .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11) :3842-3848