Catalytic C-H Arylation of Tetrathiafulvalenes for the Synthesis of Functional Materials

被引:11
|
作者
Yorimitsu, Hideki [1 ]
Yoshimura, Aya [2 ,3 ]
Misaki, Yohji [2 ,3 ,4 ]
机构
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
[2] Ehime Univ, Dept Appl Chem, Grad Sch Sci & Engn, 3 Bunkyo Cho, Matsuyama, Ehime 7908577, Japan
[3] Ehime Univ, Res Unit Power Generat & Storage Mat, Matsuyama, Ehime 7908577, Japan
[4] Ehime Univ, Res Unit Dev Organ Superconductors, Matsuyama, Ehime 7908577, Japan
来源
SYNTHESIS-STUTTGART | 2020年 / 52卷 / 22期
关键词
C-H arylation; tetrathiafulvalene; sulfur; palladium catalysis; metal-organic framework; covalent organic framework; supramolecular chemistry; redox-active material; PROTON-ABSTRACTION MECHANISM; METAL-ORGANIC FRAMEWORK; CHARGE-TRANSFER COMPLEX; CARBON-CARBON BONDS; EXTENDED-TETRATHIAFULVALENE; ELECTRICAL-CONDUCTIVITY; CRYSTAL-STRUCTURE; SUBSTITUTED TETRATHIAFULVALENE; ELECTRONIC COMMUNICATION; CONJUGATED POLYMERS;
D O I
10.1055/s-0040-1707256
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sulfur-containing functional pi-conjugated cores play key roles in materials science, mostly due to their unique electrochemical and photophysical properties. Among these, the excellent electron donor tetrathiafulvalene (TTF) has occupied a central position since the emergence of organic electronics. Peripheral C-H modification of this highly useful sulfur-containing motif has resulted in the efficient creation of new molecules that expand the applications of TTFs. This Short Review begins with the development of the palladium-catalyzed direct C-H arylation of TTF. Subsequently, it summarizes the applications of this efficient C-H transformation for the straightforward synthesis of useful TTF derivatives that are employed in a variety of research fields, demonstrating that the development of a new reaction can have a significant impact on chemical science.
引用
收藏
页码:3326 / 3336
页数:11
相关论文
共 50 条
  • [11] Catalytic C-H arylation of unactivated heteroaromatics with aryl halides by cobalt porphyrin
    Qian, Ying Ying
    Wong, Ka Lai
    Zhang, Meng Wen
    Kwok, Tsz Yiu
    To, Ching Tat
    Chan, Kin Shing
    [J]. TETRAHEDRON LETTERS, 2012, 53 (13) : 1571 - 1575
  • [12] Challenging Atroposelective C-H Arylation
    Wencel-Delord, Joanna
    Colobert, Francoise
    [J]. SYNOPEN, 2020, 04 (04): : 107 - 115
  • [13] Advance in C-H Arylation of Indoles
    Luo, Junfei
    Xu, Xing
    Zheng, Junliang
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (02) : 363 - 377
  • [14] Iridium-catalyzed C-H borylation for synthesis of functional polymer materials
    Bae, Chulsung
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [15] Catalytic Synthesis of Chiral Phosphole Oxides via Desymmetric C-H Arylation of o -Bromoaryl Phosphine Oxides
    Lin, Yan
    Ma, Wei-Yang
    Sun, Qiao-Ying
    Cui, Yu-Ming
    Xu, Li-Wen
    [J]. SYNLETT, 2017, 28 (12) : 1432 - 1436
  • [16] Fast and Selective Dehydrogenative C-H/C-H Arylation Using Niechanochemistry
    Lou, Shao-Jie
    Mao, Yang-Jie
    Xu, Dan-Qian
    He, Jiang-Qi
    Chen, Qi
    Xu, Zhen-Yuan
    [J]. ACS CATALYSIS, 2016, 6 (06): : 3890 - 3894
  • [17] Dibenzofuran Synthesis: Decarbonylative Intramolecular C-H Arylation of Aromatic Esters
    Okita, Toshimasa
    Komatsuda, Masaaki
    Saito, Ami N.
    Hisada, Tomoya
    Takahara, Tomoaki T.
    Nakayama, Keito P.
    Isshiki, Ryota
    Takise, Ryosuke
    Muto, Kei
    Yamaguchi, Junichiro
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) : 1358 - 1361
  • [18] A Concise Total Synthesis of (+)-Scholarisine A Empowered by a Unique C-H Arylation
    Smith, Myles W.
    Snyder, Scott A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (35) : 12964 - 12967
  • [19] Selective, Catalytic Oxidations of C-H Bonds in Polyethylenes Produce Functional Materials with Enhanced Adhesion
    Chen, Liye
    Malollari, Katerina G.
    Uliana, Adam
    Sanchez, Daniel
    Messersmith, Phillip B.
    Hartwig, John F.
    [J]. CHEM, 2021, 7 (01): : 137 - 145
  • [20] Toward Ideal Arene Assembly: Catalytic C-H Bond Arylation of Aromatic Compounds
    Itami, Kenichiro
    [J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2010, 68 (11) : 1132 - 1141