Synthesis of isochromenones and oxepines via Pd-catalyzed cascade cyclization of alkynes and benzynes involving C-H activation

被引:32
作者
Parthasarathy, Kanniyappan [1 ]
Han, Han [1 ]
Prakash, Chandran [1 ]
Cheng, Chien-Hong [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
关键词
HIGHLY EFFICIENT ROUTE; FUSED POLYCYCLIC AROMATICS; REGIOSELECTIVE SYNTHESIS; ARYL HALIDES; 2+2+2 CYCLOADDITION; BICYCLIC ALKENES; TERMINAL ALKYNES; FACILE SYNTHESIS; BOND ACTIVATION; PALLADIUM;
D O I
10.1039/c2cc31807e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method for the synthesis of various isochromen-6-ones and phenanthro[1,10-bc]oxepines via a palladium-catalyzed cascade carbocyclization of 2-iodobenzyl-3-phenylpropiolates and 1-iodo-2-(2-(phenylethynyl) benzyloxy) benzenes with arynes is described. The reactions involve interesting biscarbocyclization of alkynes and benzynes and C-H bond activation.
引用
收藏
页码:6580 / 6582
页数:3
相关论文
共 69 条
  • [11] Regioselective [2+2+2] cycloaddition of a nickel-benzyne complex with 1,3-diynes
    Deaton, KR
    Gin, MS
    [J]. ORGANIC LETTERS, 2003, 5 (14) : 2477 - 2480
  • [12] Organometallic generation and capture of ortho-arynes
    Dyke, Alan M.
    Hester, Alison J.
    Lloyd-Jones, Guy C.
    [J]. SYNTHESIS-STUTTGART, 2006, (24): : 4093 - 4112
  • [13] PALLADIUM-CATALYZED C-H ACTIVATION OF METHOXY GROUPS - A FACILE SYNTHESIS OF SUBSTITUTED 6H-DIBENZO[B,D]PYRANS
    DYKER, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (08): : 1023 - 1025
  • [14] A new reaction sequence involving palladium-catalyzed unsymmetrical aryl coupling
    Faccini, F
    Motti, E
    Catellani, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (01) : 78 - 79
  • [15] Synthesis of Phenanthrone Derivatives from sec-Alkyl Aryl Ketones and Aryl Halides via a Palladium-Catalyzed Dual C-H Bond Activation and Enolate Cyclization
    Gandeepan, Parthasarathy
    Parthasarathy, Kanniyappan
    Cheng, Chien-Hong
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (25) : 8569 - +
  • [16] SUPPRESSION OF ALKENE ISOMERIZATION IN PRODUCTS FROM INTRAMOLECULAR HECK REACTIONS BY ADDITION OF TL(I) SALTS
    GRIGG, R
    LOGANATHAN, V
    SANTHAKUMAR, V
    SRIDHARAN, V
    TEASDALE, A
    [J]. TETRAHEDRON LETTERS, 1991, 32 (05) : 687 - 690
  • [17] Palladium catalysed cascade alkyne-arene vinylation/alkylation approach to polyfused heterocycles.
    Grigg, R
    Loganathan, V
    Sridharan, V
    [J]. TETRAHEDRON LETTERS, 1996, 37 (19) : 3399 - 3402
  • [18] PALLADIUM-CATALYZED SYNTHESIS OF SPIROINDOLINES
    GRIGG, R
    FRETWELL, P
    MEERHOLTZ, C
    SRIDHARAN, V
    [J]. TETRAHEDRON, 1994, 50 (02) : 359 - 370
  • [19] Biaryl synthesis via palladium-catalyzed aryne multicomponent coupling
    Henderson, Jaclyn L.
    Edwards, Andrew S.
    Greaney, Michael F.
    [J]. ORGANIC LETTERS, 2007, 9 (26) : 5589 - 5592
  • [20] Three-component coupling of benzyne: Domino intermolecular carbopalladation
    Henderson, Jaclyn L.
    Edwards, Andrew S.
    Greaney, Michael F.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) : 7426 - 7427