Nickel-Catalyzed Three-Component [2+2+2] Cycloaddition Reaction of Arynes, Alkenes, and Alkynes

被引:69
作者
Qiu, Zaozao
Xie, Zuowei [1 ]
机构
[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China
关键词
arynes; cyclization; homogeneous catalysis; nickel; three-component reactions; EFFICIENT 1,2-DEHYDROCARBORANE PRECURSOR; POLYCYCLIC AROMATIC-HYDROCARBONS; RING-OPENING REACTION; TERMINAL ALKYNES; NAPHTHALENE DERIVATIVES; COUPLING REACTIONS; BICYCLIC OLEFINS; ENE REACTIONS; ACETYLENES; CARBORYNE;
D O I
10.1002/anie.200902006
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Three in one: Nickel-catalyzed three-component cycloaddition reactions of readily available arynes, activated alkenes, and alkynes gave a series of substituted 1,2-dihydronaphthalenes in moderate to very good yields with excellent chemo- and regioselectivity (see scheme, TMS=trimethylsilyl, cod=1,5-cyclooctadiene). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5729 / 5732
页数:4
相关论文
共 62 条
[1]  
[Anonymous], 2003, ANGEW CHEM
[2]   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
[3]   Reactions of 1,2-dehydro-o-carborane with thiophenes. Cycloadditions and an easy synthesis of ''benzo-o-carboranes'' [J].
BarnettThamattoor, L ;
Zheng, GX ;
Ho, DM ;
Jones, M ;
Jackson, JE .
INORGANIC CHEMISTRY, 1996, 35 (25) :7311-7315
[4]   Successive insertion of tetrafluoroethylene and CO and of tetrafluoroethylene and acetylenes into aryne-nickel(0) bonds [J].
Bennett, MA ;
Glewis, M ;
Hockless, DCR ;
Wenger, E .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (18) :3105-3114
[5]  
Bennett MA, 2001, HELV CHIM ACTA, V84, P3084
[6]   Copper-catalyzed three-component coupling of arynes, terminal alkynes and activated alkenes [J].
Bhuvaneswari, Sivakolundu ;
Jeganmohan, Masilamani ;
Cheng, Chien-Hong .
CHEMICAL COMMUNICATIONS, 2008, (40) :5013-5015
[7]   Palladium-catalyzed three-component coupling of arynes with allylic acetates or halides and terminal alkynes promoted by cuprous iodide [J].
Bhuvaneswari, Sivakolundu ;
Jeganmohan, Masilamani ;
Yang, Ming-Che ;
Cheng, Chien-Hong .
CHEMICAL COMMUNICATIONS, 2008, (18) :2158-2160
[8]   Carbocyclization of aromatic iodides, bicyclic alkenes, and benzynes involving a palladium-catalyzed C-H bond activation as a key step [J].
Bhuvaneswari, Sivakolundu ;
Jeganmohan, Masilamani ;
Cheng, Chien-Hong .
ORGANIC LETTERS, 2006, 8 (24) :5581-5584
[9]   REACTION OF 1,2-DEHYDRO-O-CARBORANE WITH ACETYLENES - ENE REACTIONS AND CYCLOADDITION TO GIVE AN ANALOG OF BENZOCYCLOBUTADIENE [J].
CUNNINGHAM, RJ ;
BIAN, NY ;
JONES, M .
INORGANIC CHEMISTRY, 1994, 33 (22) :4811-4812
[10]   Synthesis, structure, and reactivity of a zirconocene-carboryne precursor [J].
Deng, L ;
Chan, HS ;
Xie, ZW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (40) :13774-13775