Ir-catalyzed C-H silylations of phenyldeazapurines

被引：8
|
作者：
Sabat, Nazarii [1 ,2 ]
Slavetinska, Lenka Postova [2 ]
Hocek, Michal [1 ,2 ]
机构：
[1] Charles Univ Prague, Fac Sci, Dept Organ Chem, CZ-12843 Prague 2, Czech Republic
[2] Acad Sci Czech Republ, Gilead & IOCB Res Ctr, Inst Organ Chem & Biochem, CZ-16610 Prague 6, Czech Republic
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 49期
关键词：
C-H silylation; Deazapurines; Iridium catalysis; C-H activations; CROSS-COUPLING REACTIONS; CYTOSTATIC ACTIVITY; DEHYDROGENATIVE SILYLATION; 6-ARYLPURINE NUCLEOSIDES; PYRIMIDINE NUCLEOSIDES; SUZUKI; ARYLATION; PURINES; FUNCTIONALIZATION; 6-PHENYLPURINE;
D O I：
10.1016/j.tetlet.2015.10.089
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A study of the Ir-catalyzed C-H silylation of 6-phenyl-7-deazapurines or -9-deazapurines with trialkylsilanes revealed that this reaction preferentially proceeded via ortho-silylation at the aryl group due to the directing effect of the N1 nitrogen of the deazapurine, rather than C-H silylation at the heterocycle which was only a minor side-reaction. A preparative protocol for the ortho-silylation of aryldeazapurines is. presented. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6860 / 6862
页数：3
相关论文
共 50 条
  • [1] Ir-Catalyzed Functionalization of C-H Bonds
    Choi, Jongwook
    Goldman, Alan S.
    IRIDIUM CATALYSIS, 2011, 34 : 139 - 167
  • [2] Ir-Catalyzed C-H Amidation and Borylation of Anthraquinones
    Camelio, Andrew M.
    Wright, Robert J.
    Knight, Nicole T.
    Jazdzewski, Brian A.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (08): : 4940 - 4947
  • [3] Atroposelective Ir-Catalyzed C-H Borylation of Phthalazine Heterobiaryls
    Stehrer, Paul
    Spannenberg, Anke
    Hapke, Marko
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (19): : 14222 - 14226
  • [4] Ir-catalyzed proximal and distal C-H borylation of arenes
    Haldar, Chabush
    Hoque, Md Emdadul
    Chaturvedi, Jagriti
    Hassan, Mirja Md Mahamudul
    Chattopadhyay, Buddhadeb
    CHEMICAL COMMUNICATIONS, 2021, 57 (97) : 13059 - 13074
  • [5] Ir-Catalyzed Enantioselective, Intramolecular Silylation of Methyl C-H Bonds
    Su, Bo
    Hartwig, John F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (35) : 12137 - 12140
  • [6] Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization
    Yang, Qi-Liang
    Xing, Yi-Kang
    Wang, Xiang-Yang
    Ma, Hong-Xing
    Weng, Xin-Jun
    Yang, Xiang
    Guo, Hai-Ming
    Mei, Tian-Sheng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (48) : 18970 - 18976
  • [7] Microwave-assisted, Ir-catalyzed aromatic C-H borylation
    Li Zeqing
    Liang Zhibin
    Wang Yuqiang
    Yu Pei
    RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (04) : 1917 - 1926
  • [8] Boc Groups as Protectors and Directors for Ir-Catalyzed C-H Borylation of Heterocycles
    Kallepalli, Venkata A.
    Shi, Feng
    Paul, Sulagna
    Onyeozili, Edith N.
    Maleczka, Robert E., Jr.
    Smith, Milton R., III
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (23): : 9199 - 9201
  • [9] Ir-Catalyzed C-H Amidation of Aldehydes with Stoichiometric/Catalytic Directing Group
    Zhang, Yun-Fei
    Wu, Bin
    Shi, Zhang-Jie
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (49) : 17808 - 17812
  • [10] Ir-Catalyzed Ortho-Selective C-H Borylation of Difluoromethyl Arenes
    Li, Chen-Yuan
    Zhang, Zengyu
    Yan, Xiaoyu
    ORGANIC LETTERS, 2023, 25 (40) : 7278 - 7282
12345