Selective Synthesis of [12]Cycloparaphenylene

被引:403
作者
Takaba, Hiroko [1 ]
Omachi, Haruka [1 ]
Yamamoto, Yosuke [1 ]
Bouffard, Jean [1 ]
Itami, Kenichiro [1 ]
机构
[1] Nagoya Univ, Grad Sch Sci, Dept Chem, Chikusa Ku, Nagoya, Aichi 4648602, Japan
关键词
aromaticity; cross-coupling; cycloparaphenylenes; macrocyclization; palladium; NONPLANAR AROMATIC-COMPOUNDS; CROSS-COUPLING REACTIONS; TUBE-SHAPED MOLECULES; DOUBLE-STRANDED CYCLE; H BOND ARYLATION; BELT REGION; ORGANOBORON COMPOUNDS; ARYLBORONIC ACIDS; CARBON SKELETON; PI-SYSTEMS;
D O I
10.1002/anie.200902617
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tighten your belt: [12]Cycloparaphenylene, the sidewall segment of a carbon nanotube (see picture), has been synthesized in a selective manner through stepwise palladium-catalyzed coupling reactions. The synthesis capitalizes on the ability of the cis-1,4-dihydroxycyclohexane- 1,4-diyl unit to attenuate the build-up of strain energy during macrocyclization. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6112 / 6116
页数:5
相关论文
共 91 条
  • [1] Nanotubes from carbon
    Ajayan, PM
    [J]. CHEMICAL REVIEWS, 1999, 99 (07) : 1787 - 1799
  • [2] [Anonymous], 2009, ANGEW CHE
  • [3] Reduction of strained polycycles: How much strain can a pyrene anion take?
    Aprahamian, I
    Bodwell, GJ
    Fleming, JJ
    Manning, GP
    Mannion, MR
    Merner, BL
    Sheradsky, T
    Vermeij, RJ
    Rabinovitz, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) : 6765 - 6775
  • [4] MOLECULAR BELTS .2. SUBSTRATE-DIRECTED SYNTHESES OF BELT-TYPE AND CAGE-TYPE STRUCTURES
    ASHTON, PR
    GIRRESER, U
    GIUFFRIDA, D
    KOHNKE, FH
    MATHIAS, JP
    RAYMO, FM
    SLAWIN, AMZ
    STODDART, JF
    WILLIAMS, DJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) : 5422 - 5429
  • [5] MOLECULAR LEGO .1. SUBSTRATE-DIRECTED SYNTHESIS VIA STEREOREGULAR DIELS-ALDER OLIGOMERIZATIONS
    ASHTON, PR
    BROWN, GR
    ISAACS, NS
    GIUFFRIDA, D
    KOHNKE, FH
    MATHIAS, JP
    SLAWIN, AMZ
    SMITH, DR
    STODDART, JF
    WILLIAMS, DJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) : 6330 - 6353
  • [6] Copper-mediated C-H bond arylation of arenes with arylboronic acids
    Ban, Ikuya
    Sudo, Tomoko
    Taniguchi, Tadashi
    Itami, Kenichiro
    [J]. ORGANIC LETTERS, 2008, 10 (16) : 3607 - 3609
  • [7] Billingsley K.L., 2006, Angew. Chem, V118, P3564
  • [8] A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds
    Billingsley, Kelvin L.
    Anderson, Kevin W.
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (21) : 3484 - 3488
  • [9] Bodwell G. J., 1996, ANGEW CHEM, V108, P1418
  • [10] 1,8-dioxa[8](2,7)pyrenophane, a severely distorted polycyclic aromatic hydrocarbon
    Bodwell, GJ
    Bridson, JN
    Houghton, TJ
    Kennedy, JWJ
    Mannion, MR
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (12): : 1320 - 1321