Remote meta C-H bond functionalization of 2-phenethylsulphonic acid and 3-phenylpropanoic acid derivatives

被引:53
作者
Modak, Atanu [1 ]
Mondal, Anirban [1 ]
Watile, Rahul [1 ]
Mukherjee, Semanti [1 ]
Maiti, Debabrata [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
关键词
ELECTRON-DEFICIENT ARENES; DIRECTING GROUP; CONJUGATED POLYMERS; ACTIVATION; OLEFINATION; ARYLATION; TEMPLATE; BORYLATION; LIGAND; SELECTIVITY;
D O I
10.1039/c6cc08302a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This discovery illustrates selective meta C-H bond activation from multiple non-equivalent C-H bonds present in medicinally relevant arylethanesulfonic acid and the 2-arylpropanoic acid moiety using weakly coordinating nitrile as a directing group. Transformation of the meta olefinated compounds to important organic molecules has been demonstrated. Efforts were made to obtain mechanistic detail of the meta C-H bond functionalization reaction.
引用
收藏
页码:13916 / 13919
页数:4
相关论文
共 58 条
  • [21] Mild metal-catalyzed C-H activation: examples and concepts
    Gensch, T.
    Hopkinson, M. N.
    Glorius, F.
    Wencel-Delord, J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (10) : 2900 - 2936
  • [22] Synthesis of Light-Emitting Conjugated Polymers for Applications in Electroluminescent Devices
    Grimsdale, Andrew C.
    Chan, Khai Leok
    Martin, Rainer E.
    Jokisz, Pawel G.
    Holmes, Andrew B.
    [J]. CHEMICAL REVIEWS, 2009, 109 (03) : 897 - 1091
  • [23] meta-Selective C-H Bond Alkylation with Secondary Alkyl Halides
    Hofmann, Nora
    Ackermann, Lutz
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (15) : 5877 - 5884
  • [24] Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate
    Ishiyama, T
    Takagi, J
    Ishida, K
    Miyaura, N
    Anastasi, NR
    Hartwig, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) : 390 - 391
  • [25] USE OF SAMARIUM DIIODIDE AS AN ALTERNATIVE TO SODIUM MERCURY AMALGAM IN THE JULIA-LYTHGOE OLEFINATION
    KECK, GE
    SAVIN, KA
    WEGLARZ, MA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) : 3194 - 3204
  • [26] Kuninobu Y, 2015, NAT CHEM, V7, P712, DOI [10.1038/NCHEM.2322, 10.1038/nchem.2322]
  • [27] Meta-Selective C-H Functionalization Using a Nitrile-Based Directing Group and Cleavable Si-Tether
    Lee, Sunggi
    Lee, Hyelee
    Tan, Kian L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (50) : 18778 - 18781
  • [28] Activation of remote meta-C-H bonds assisted by an end-on template
    Leow, Dasheng
    Li, Gang
    Mei, Tian-Sheng
    Yu, Jin-Quan
    [J]. NATURE, 2012, 486 (7404) : 518 - 522
  • [29] N-Acyl Amino Acid Ligands for Ruthenium(II)-Catalyzed meta-C-H tert-Alkylation with Removable Auxiliaries
    Li, Jie
    Warratz, Svenja
    Zell, Daniel
    De Sarkar, Suman
    Ishikawa, Eloisa Eriko
    Ackermann, Lutz
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (43) : 13894 - 13901
  • [30] Pd(II)-catalysed meta-C-H functionalizations of benzoic acid derivatives
    Li, Shangda
    Cai, Lei
    Ji, Huafang
    Yang, Long
    Li, Gang
    [J]. NATURE COMMUNICATIONS, 2016, 7