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
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
  • [41] Noncovalent Interactions in Ir-Catalyzed C-H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters
    Hoque, Md Emdadul
    Bisht, Ranjana
    Haldar, Chabush
    Chattopadhyay, Buddhadeb
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (23) : 7745 - 7748
  • [42] Ir-Catalyzed Cross-Coupling of Styrene Derivatives with Allylic Carbonates: Free Amine Assisted Vinyl C-H Bond Activation
    He, Hu
    Liu, Wen-Bo
    Dai, Li-Xin
    You, Shu-Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (24) : 8346 - +
  • [43] Ir-catalyzed C–S coupling of quinones with sulfonyl chloride
    Long Wang
    Yi-Bi Xie
    Quan-Li Yang
    Ming-Guo Liu
    Kai-Bo Zheng
    Yu-lin Hu
    Nian-Yu Huang
    Journal of the Iranian Chemical Society, 2016, 13 : 1797 - 1803
  • [44] Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C-H Borylation/N-C(O) Activation
    Gao, Pengcheng
    Szostak, Michal
    ORGANIC LETTERS, 2020, 22 (15) : 6010 - 6015
  • [45] Ir-Catalyzed Distal Branch-Selective Hydroarylation of Unactivated Internal Alkenes with Benzanilides via C-H Activation along with Consecutive Isomerization
    Tang, King Hung Nigel
    Tokutake, Ryo
    Ito, Mamoru
    Shibata, Takanori
    ORGANIC LETTERS, 2023, 25 (28) : 5197 - 5202
  • [46] Control of meta-selectivity in the Ir-catalyzed aromatic C-H borylation directed by hydrogen bond interaction: A combined computational and experimental study
    Wenju Chang
    Yajun Wang
    Yu Chen
    Jiawei Ma
    Yong Liang
    ChineseChemicalLetters, 2023, 34 (05) : 294 - 298
  • [47] Enantioselective Cross-Coupling of Electron-Deficient Alkenes via Ir-Catalyzed Vinylic sp2 C-H Alkylation
    Shibata, Takanori
    Kojima, Masafumi
    Onoda, Sahoko
    Ito, Mamoru
    ORGANIC LETTERS, 2021, 23 (21) : 8158 - 8162
  • [48] Ir catalyzed regioselective C-H borylation of arenes and the scale up
    Li, Xiaoyong
    Oppenheimer, Jossian
    Li, Hao
    Jayasundara, Chathurika
    Maleczka, Robert
    Smith, Milton
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [49] Ir(iii)-catalyzed thioether directed arene C-H alkenylation
    Li, Chen
    Chen, Xian
    Bao, Rui-Peng
    Li, Dong-Li
    Zhang, Kun
    Wang, Dong-Hui
    RSC ADVANCES, 2019, 9 (52) : 30134 - 30138
  • [50] Ir-catalyzed enantioselective allylation of enamines
    Weix, Daniel J.
    Hartwig, John F.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233