Hypervalent iodine(III)-mediated C(sp3)-H bond arylation, alkylation, and amidation of isothiochroman

被引:11
|
作者
Muramatsu, Wataru [1 ]
Nakano, Kimihiro [1 ]
机构
[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan
关键词
Isothiochroman; C-H activation; Hypervalent iodine; Arylation; Alkylation; Amidation; THIOBENZOPHENONE; CHEMISTRY; OXIDATION; TETRAHYDROISOQUINOLINES;
D O I
10.1016/j.tetlet.2014.11.134
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have developed a one-step method for introducing aryl, alkyl, and amide groups at the C(1)-position of isothiochromans via an oxidation reaction using hypervalent iodine(III), [bis(trifluoroacetoxy) iodo]benzene (PIFA), followed by an nucleophilic addition reaction using Grignard reagents and an amide. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:437 / 440
页数:4
相关论文
共 50 条
  • [21] sp3 C-H bond arylation directed by amidine protecting group:: α-arylation of pyrrolidines and piperidines
    Pastine, Stefan J.
    Gribkov, Denis V.
    Sames, Dalibor
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (44) : 14220 - 14221
  • [22] Rhodium(III)-catalyzed Intermolecular Unactivated Secondary C(sp3)-H Bond Amidation Directed by 3,5-dimethylpyrazole
    Wang, Yanwei
    Liu, Hongxin
    Li, Bin
    Wang, Baiquan
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (07) : 1564 - 1569
  • [23] Thiochromane Formation via Visible-Light-Mediated Intramolecular ?-C(sp3)-H Bond Arylation of Sulfonamides
    Liu, Shuai
    Kumar, Nivesh
    Robert, Frederic
    Landais, Yannick
    ORGANIC LETTERS, 2023, 25 (17) : 3072 - 3077
  • [24] A Catalytic Alkylation of Ketones via sp3 C-H Bond Activation
    Peng, Xue
    Hirao, Yuki
    Yabu, Shunsuke
    Sato, Hirofumi
    Higashi, Masahiro
    Akai, Takuya
    Masaoka, Shigeyuki
    Mitsunuma, Harunobu
    Kanai, Motomu
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (10): : 6333 - 6346
  • [25] Electrochemical Benzylic C(sp3)-H Direct Amidation
    Choi, Anthony
    Goodrich, Oliver H.
    Atkins, Alexander P.
    Edwards, Matthew D.
    Tiemessen, David
    George, Michael W.
    Lennox, Alastair J. J.
    ORGANIC LETTERS, 2024, 26 (03) : 653 - 657
  • [26] Selective C(sp3)-C(sp3) Cleavage/Alkynylation of Cycloalkylamides Enables Aminoalkyne Synthesis with Hypervalent Iodine Reagents
    Liu, Zhengyi
    Wu, Shuang
    Chen, Yiyun
    ACS CATALYSIS, 2021, 11 (16) : 10565 - 10573
  • [27] Carbon Dioxide-Mediated C(sp3)-H Arylation of Amine Substrates
    Kapoor, Mohit
    Liu, Daniel
    Young, Michael C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (22) : 6818 - 6822
  • [28] Iodine-Mediated δ-Amination of sp3 C-H Bonds
    Ye, Wenjun
    Xiong, Hanyu
    Wang, Manman
    Chang, Junbiao
    Yu, Wenquan
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (05): : 3481 - 3490
  • [29] Rhodium(III)-Catalyzed Intermolecular Amidation with Azides via C(sp3)-H Functionalization
    Wang, Nuancheng
    Li, Renhe
    Li, Liubo
    Xu, Shansheng
    Song, Haibin
    Wang, Baiquan
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11): : 5379 - 5385
  • [30] Direct Formation of C-C, C-N, and C-O Bonds in Dihydroquinazolines via Hypervalent Iodine(III)-Mediated sp3 C-H Functionalization
    Carlson, Haley M.
    Smith, Sydney R.
    Mosey, R. Adam
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (02): : 1160 - 1174