Imposing curvature on a polyarene by intramolecular palladium-catalyzed arylation reactions:: A simple synthesis of dibenzo[a,g]corannulene

被引:112
作者
Reisch, HA [1 ]
Bratcher, MS [1 ]
Scott, LT [1 ]
机构
[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA
关键词
D O I
10.1021/ol005755p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Palladium catalysis has been found to offer an effective solution phase alternative to gas phase flash vacuum pyrolysis as a method for converting the planar ring system of 7,10-di(2-bromophenyl)fluoranthene (4) to that of the C28H14 bowl-shaped fullerene fragment dibenzo[a,g]corannulene (5).
引用
收藏
页码:1427 / 1430
页数:4
相关论文
共 38 条
  • [11] 2-5
  • [12] A CONCISE TOTAL SYNTHESIS OF THE AGLYCONE OF THE GILVOCARCINS
    DESHPANDE, PP
    MARTIN, OR
    [J]. TETRAHEDRON LETTERS, 1990, 31 (44) : 6313 - 6316
  • [13] TRANSITION-METAL-CATALYZED ANNULATION REACTIONS .7. PALLADIUM-CATALYZED C-H ACTIVATION AT METHOXY GROUPS - REGIOCHEMISTRY OF THE DOMINO COUPLING PROCESSES
    DYKER, G
    [J]. CHEMISCHE BERICHTE, 1994, 127 (04) : 739 - 742
  • [14] Synthesis of 'crushed fullerene' C60H30
    Gómez-Lor, B
    de Frutos, O
    Echavarren, AM
    [J]. CHEMICAL COMMUNICATIONS, 1999, (23) : 2431 - 2432
  • [15] Synthesis of spiro polycyclic aromatic hydrocarbons by intramolecular palladium-catalyzed arylation
    Gonzalez, JJ
    Garcia, N
    GomezLor, B
    Echavarren, AM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) : 1286 - 1291
  • [16] PALLADACYCLES AS STRUCTURALLY DEFINED CATALYSTS FOR THE HECK OLEFINATION OF CHLOROARENES AND BROMOARENES
    HERRMANN, WA
    BROSSMER, C
    OFELE, K
    REISINGER, CP
    PRIERMEIER, T
    BELLER, M
    FISCHER, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17): : 1844 - 1848
  • [17] TOTAL SYNTHESIS OF THE GILVOCARCINS
    HOSOYA, T
    TAKASHIRO, E
    MATSUMOTO, T
    SUZUKI, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) : 1004 - 1015
  • [18] FORMATION ENTHALPY OF CORANNULENE - MICROBOMB COMBUSTION CALORIMETRY
    KIYOBAYASHI, T
    NAGANO, Y
    SAKIYAMA, M
    YAMAMOTO, K
    CHENG, PC
    SCOTT, LT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (11) : 3270 - 3271
  • [19] Heck reactions in the presence of p(t-bu)3:: Expanded scope and milder reaction conditions for the coupling of aryl chlorides
    Littke, AF
    Fu, GC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) : 10 - 11
  • [20] Synthetic studies directed towards bucky-balls and bucky-bowls
    Mehta, G
    Rao, HSP
    [J]. TETRAHEDRON, 1998, 54 (44) : 13325 - 13370