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
  • [1] AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes
    Asao, N
    Takahashi, K
    Lee, S
    Kasahara, T
    Yamamoto, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) : 12650 - 12651
  • [2] IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores
    Barluenga, J
    Trincado, M
    Rubio, E
    González, JM
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) : 2406 - 2409
  • [3] Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles:: A versatile trigger for assembling oxygen heterocycles
    Barluenga, J
    Vázquez-Villa, H
    Ballesteros, A
    González, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) : 9028 - 9029
  • [4] REGIOSELECTIVE AND STEREOSELECTIVE IODOFLUORINATION OF ALKENES WITH BIS(PYRIDINE)IODONIUM(I) TETRAFLUOROBORATE
    BARLUENGA, J
    CAMPOS, PJ
    GONZALEZ, JM
    SUAREZ, JL
    ASENSIO, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) : 2234 - 2237
  • [5] Reactions of (tert-butyldimethylsilyl) alkynes with IPy2BF4: Selective synthesis of novel head-to-head dimers
    Barluenga, J
    Llorente, I
    AlvarezGarcia, LJ
    Gonzalez, JM
    Campos, PJ
    Diaz, MR
    GarciaGranda, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (29) : 6933 - 6934
  • [6] ELECTROPHILIC ADDITIONS OF POSITIVE IODINE TO ALKYNES THROUGH AN IODONIUM MECHANISM
    BARLUENGA, J
    RODRIGUEZ, MA
    CAMPOS, PJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) : 3104 - 3106
  • [7] A reiterative approach to 2,3-disubstituted naphthalenes and anthracenes
    Bowles, DM
    Anthony, JE
    [J]. ORGANIC LETTERS, 2000, 2 (01) : 85 - 87
  • [8] REGIO-CONTROLLED ENE-YNE PHOTOCHEMICAL [2+2] CYCLOADDITION USING SILICON AS A TETHER
    BRADFORD, CL
    FLEMING, SA
    WARD, SC
    [J]. TETRAHEDRON LETTERS, 1995, 36 (24) : 4189 - 4192
  • [9] An approach to the synthesis of the benzo[b]fluorene core of the kinamycins by an arylalkyne-allene cycloaddition
    deFrutos, O
    Echavarren, AM
    [J]. TETRAHEDRON LETTERS, 1997, 38 (45) : 7941 - 7942
  • [10] Synthesis of substituted naphthalenes by the palladium-catalyzed annulation of internal alkynes
    Huang, QH
    Larock, RC
    [J]. ORGANIC LETTERS, 2002, 4 (15) : 2505 - 2508