Palladium-Catalyzed Direct C(sp2)-H Cyanomethylation of Arylamides using Chloroacetonitrile

被引:0
作者
Garai, Sumit [1 ]
Sureshkumar, Devarajulu [1 ]
机构
[1] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741246, West Bengal, India
关键词
C-H BOND; ARYLATION; ALKYLATION; FUNCTIONALIZATION; COORDINATION; SILVER; ARENES; ROLES;
D O I
10.1021/acs.joc.3c01431
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this study, we devised a palladium-catalyzed efficient and versatile method for C-(sp(2))-H ortho-cyanomethylation of arylamides with a broad substrate scope and moderate to excellent yields. An inexpensive and commercially available chloroacetonitrile was employed as a cyanomethylating source. This method is also compatible with the air atmosphere. Further, the synthetic feasibility of this technique is established by gram-scale synthesis and functional group transformation of the products.
引用
收藏
页码:12755 / 12764
页数:10
相关论文
共 35 条
  • [1] Palladium(II)-Catalyzed Direct Alkoxylation of Arenes: Evidence for Solvent-Assisted Concerted Metalation Deprotonation
    Anand, Megha
    Sunoj, Raghavan B.
    [J]. ORGANIC LETTERS, 2011, 13 (18) : 4802 - 4805
  • [2] Multiple roles of silver salts in palladium-catalyzed C-H activations
    Bay, Katherine L.
    Yang, Yun-Fang
    Houk, K. N.
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 864 : 19 - 25
  • [3] Synthesis of ortho-arylated/benzylated arylacetamide derivatives: Pd(OAc)2-catalyzed bidentate ligand-aided arylation and benzylation of the γ-C-H bond of arylacetamides
    Bisht, Narendra
    Babu, Srinivasarao Arulananda
    [J]. TETRAHEDRON, 2016, 72 (39) : 5886 - 5897
  • [4] Fatiadi A.J., 1983, Triple-Bonded Functional Groups, V2
  • [5] Fatiadi A.J., 1983, TRIPLE BONDED FUNCTI, P1057, DOI DOI 10.1002/9780470771709.CH9
  • [6] Nitrile-Containing Pharmaceuticals: Efficacious Roles of the Nitrile Pharmacophore
    Fleming, Fraser F.
    Yao, Lihua
    Ravikumar, P. C.
    Funk, Lee
    Shook, Brian C.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (22) : 7902 - 7917
  • [7] Diastereoselective palladium-catalyzed C(sp3)-H cyanomethylation of amino acid and carboxylic acid derivatives
    Garai, Sumit
    Ghosh, Krishna Gopal
    Biswas, Ashik
    Chowdhury, Sushobhan
    Sureshkumar, Devarajulu
    [J]. CHEMICAL COMMUNICATIONS, 2022, 58 (56) : 7793 - 7796
  • [8] Palladium-Catalyzed Transformations of Alkyl C-H Bonds
    He, Jian
    Wasa, Masayuki
    Chan, Kelvin S. L.
    Shao, Ojan
    Yu, Jin-Quan
    [J]. CHEMICAL REVIEWS, 2017, 117 (13) : 8754 - 8786
  • [9] The Pd-catalyzed C-H alkylation of ortho-methyl-substituted aromatic amides with maleimide occurs preferentially at the ortho-methyl C-H bond over the ortho-C-H bond
    He, Qiyuan
    Ano, Yusuke
    Chatani, Naoto
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (67) : 9983 - 9986
  • [10] Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds
    Liu, Bin
    Romine, Andrew M.
    Rubel, Camille Z.
    Engle, Keary M.
    Shi, Bing-Feng
    [J]. CHEMICAL REVIEWS, 2021, 121 (24) : 14957 - 15074