Convergent Synthesis of Fluorene Derivatives by a Rhodium-Catalyzed Stitching Reaction/Alkene Isomerization Sequence

被引：16
作者：
Nishida, Masaki [1 ]
Shintani, Ryo [1 ]
机构：
[1] Osaka Univ, Grad Sch Engn Sci, Dept Mat Engn Sci, Div Chem, Toyonaka, Osaka 5608531, Japan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 31期
关键词：
fluorene; isomerization; rhodium; stitching reaction; pi-conjugated compounds; ARYLBORONIC ACIDS; SUBSTITUTED FLUORENES; C-H; ASYMMETRIC ARYLATION; EFFICIENT SYNTHESIS; CRAFTS REACTIONS; CYCLIZATION; COMPLEXES; ALDEHYDES; ALKYNES;
D O I：
10.1002/chem.201901519
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A convergent synthetic method for the synthesis of fluorene derivatives has been developed by devising a rhodium-catalyzed stitching reaction/alkene isomerization sequence. The reactions proceed smoothly under mild conditions for a variety of substrate combinations, and extended pi-conjugation systems are also readily accessible by utilizing this synthetic method. Optical properties of the obtained fluorene derivatives have also been examined.
引用
收藏
页码：7475 / 7479
页数：5
相关论文
共 87 条
  • [1] Fluorene-Based Materials and Their Supramolecular Properties
    Abbel, Robert
    Schenning, Albertus P. H. J.
    Meijer, E. W.
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2009, 47 (17) : 4215 - 4233
  • [2] Iron-Catalyzed Tandem Conia-Ene/Friedel-Crafts Reactions of o-Alkynyldihydrochalcones: Access to Benzo[b]fluorenes
    Akbar, Sikkandarkani
    Srinivasan, Kannupal
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (03) : 1229 - 1236
  • [3] Alt HG, 1998, CHEM SOC REV, V27, P323
  • [4] [Anonymous], 2012, ANGEW CHEM
  • [5] Rhodium catalysed chemo- and stereoselective arylative and alkenylative cyclisation reactions of unsymmetric diynes containing a terminal alkyne moiety with organoboronic acids
    Artok, Levent
    Kus, Melih
    Urer, Bagdagul N.
    Turkmen, Gulsah
    Aksin-Artok, Ozge
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (09) : 2060 - 2067
  • [6] Copper-Catalyzed Coupling of N-Tosylhydrazones with Amines: Synthesis of Fluorene Derivatives
    Aziz, Jessy
    Frison, Gilles
    Gomez, Montserrat
    Brion, Jean-Daniel
    Hamze, Abdallah
    Alami, Mouad
    [J]. ACS CATALYSIS, 2014, 4 (12): : 4498 - 4503
  • [7] Potassium alkenyl- and aryltrifluoroborates: Stable and efficient agents for rhodium-catalyzed addition to aldehydes and enones
    Batey, RA
    Thadani, AN
    Smil, DV
    [J]. ORGANIC LETTERS, 1999, 1 (10) : 1683 - 1686
  • [8] Fluorene-based polymers-preparation and applications
    Bernius, M
    Inbasekaran, M
    Woo, E
    Wu, WS
    Wujkowski, L
    [J]. JOURNAL OF MATERIALS SCIENCE-MATERIALS IN ELECTRONICS, 2000, 11 (02) : 111 - 116
  • [9] Berthon-Gelloz G, 2011, BORONIC ACIDS, VOL 2: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS, MEDICINE AND MATERIALS, 2ND EDITION, P263
  • [10] A room-temperature protocol for the rhodium(I)-catalyzed addition of arylboron compounds to sulfinimines
    Bolshan, Y
    Batey, RA
    [J]. ORGANIC LETTERS, 2005, 7 (08) : 1481 - 1484
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