Regioselective synthesis of substituted naphthalenes:: A novel de novo approach based on a metal-free protocol for stepwise cycloaddition of o-alkynylbenzaldehyde derivatives with either alkynes or alkenes

被引:134
作者
Barluenga, J [1 ]
Váquez-Villa, H [1 ]
Ballesteros, A [1 ]
González, JM [1 ]
机构
[1] Univ Oviedo, Inst Quim Organomet Enrique Moles, Unidad Asociada, CSIC, E-33006 Oviedo, Spain
关键词
D O I
10.1021/ol035691t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] Iodonium ions, o-alkynyl-substituted carbonyl compounds, and alkynes react to give 1-iodonaphthalene derivatives featuring interesting substitution patterns. The reaction with alkenes instead of acetylenes affords related naphthyl ketone derivatives. These two metal-free processes are conducted at room temperature and furnish products in a regioselective manner.
引用
收藏
页码:4121 / 4123
页数:3
相关论文
共 20 条
  • [11] Kuznetsov E. V., 1990, ADV HETEROCYCL CHEM, V50, P157, DOI [10.1016/S0065-2725(08)60063-X, DOI 10.1016/S0065-2725(08)60063-X]
  • [12] Reactions of iodinated vinylidene complexes generated from 1-iodo-1-alkynes and W(CO)5(thf)
    Miura, T
    Iwasawa, N
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (04) : 518 - 519
  • [13] Palladium-catalyzed cocyclization of arynes with alkynes:: Selective synthesis of phenanthrenes and naphthalenes
    Peña, D
    Pérez, D
    Guitián, E
    Castedo, L
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) : 5827 - 5828
  • [14] Strained intermediates in intramolecular dehydro Diels-Alder reactions:: Rearrangement of cyclic allenes via 1,2-dehydro[10]annulenes
    Rodríguez, D
    Navarro-Vázquez, A
    Castedo, L
    Domínguez, D
    Saá, C
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) : 9178 - 9179
  • [15] Cyclic allene intermediates in intramolecular dehydro Diels-Alder reactions:: Labeling and theoretical cycloaromatization studies
    Rodríguez, D
    Navarro-Vázquez, A
    Castedo, L
    Domínguez, D
    Saá, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) : 1938 - 1946
  • [16] Coupling reaction of zirconacyclopentadienes with dihalonaphthalenes and dihalopyridines: A new procedure for the preparation of substituted anthracenes, quinolines, and isoquinolines
    Takahashi, T
    Li, YZ
    Stepnicka, P
    Kitamura, M
    Liu, YJ
    Nakajima, K
    Kotora, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (04) : 576 - 582
  • [17] Copper-mediated coupling of zirconacyclopentadienes with dihalo aromatic compounds. Formation of fused aromatic rings
    Takahashi, T
    Hara, R
    Nishihara, Y
    Kotora, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) : 5154 - 5155
  • [18] Viswanathan GS, 2002, ANGEW CHEM INT EDIT, V41, P2138, DOI 10.1002/1521-3773(20020617)41:12<2138::AID-ANIE2138>3.0.CO
  • [19] 2-T
  • [20] Iridium-catalyzed reaction of aroyl chlorides with internal alkynes to produce substituted naphthalenes and anthracenes
    Yasukawa, T
    Satoh, T
    Miura, M
    Nomura, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) : 12680 - 12681