Gold(I) or gold(III) as active species in AuCl3-catalyzed cyclization/cycloaddition reactions?: A DFT study

被引:108
作者
Straub, BF [1 ]
机构
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
关键词
D O I
10.1039/b404876h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In a B3LYP mechanistic study, AuCl and AuCl3 catalysts feature similar overall barriers for a reaction sequence of 2-ethynyl benzaldehyde and ethyne to 1-naphthyl carbaldehyde, comprising cyclization, [3+2] cycloaddition, and two rearrangements.
引用
收藏
页码:1726 / 1728
页数:3
相关论文
共 60 条
  • [1] AuBr3-catalyzed cyclization of o-(alkynyl)nitrobenzenes.: Efficient synthesis of isatogens and anthranils
    Asao, N
    Sato, K
    Yamamoto, Y
    [J]. TETRAHEDRON LETTERS, 2003, 44 (30) : 5675 - 5677
  • [2] Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes
    Asao, N
    Nogami, T
    Lee, S
    Yamamoto, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) : 10921 - 10925
  • [3] 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
  • [4] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
    BECKE, AD
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
  • [5] Organometallic gold(III) compounds as catalysts for the addition of water and methanol to terminal alkynes
    Casado, R
    Contel, M
    Laguna, M
    Romero, P
    Sanz, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) : 11925 - 11935
  • [6] EFFICIENT DIFFUSE FUNCTION-AUGMENTED BASIS SETS FOR ANION CALCULATIONS. III. THE 3-21+G BASIS SET FOR FIRST-ROW ELEMENTS, LI-F
    CLARK, T
    CHANDRASEKHAR, J
    SPITZNAGEL, GW
    SCHLEYER, PV
    [J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1983, 4 (03) : 294 - 301
  • [7] Dyker G, 2000, ANGEW CHEM INT EDIT, V39, P4237, DOI 10.1002/1521-3773(20001201)39:23<4237::AID-ANIE4237>3.0.CO
  • [8] 2-A
  • [9] Gold(III) chloride-catalyzed addition reactions of electron-rich arenes to methyl vinyl ketone
    Dyker, G
    Muth, E
    Hashmi, ASK
    Ding, L
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (11) : 1247 - 1252
  • [10] Gold(III) chloride catalyzed domino processes with isobenzopyrylium cation intermediates
    Dyker, G
    Hildebrandt, D
    Liu, JH
    Merz, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (36) : 4399 - 4402