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
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 02期
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
  • [41] Iodine(III)-Mediated Trifluoroacetylation of a C(sp2)-H or C(sp)-H Bond with Masked Trifluoroacyl Reagents
    Ye, Zhi-Peng
    Guo, Meng
    Ye, Yong-Qing
    Yuan, Chu-Ping
    Wang, Hai-Long
    Yang, Jing-Song
    Chen, Hong-Bin
    Xiang, Hao-Yue
    Chen, Kai
    Yang, Hua
    ORGANIC LETTERS, 2024, 26 (24) : 5196 - 5201
  • [42] Direct and Efficient C(sp3)-H Bond Alkylation of Tetrahydroisoquinolines and Isochroman with Alkylzinc Reagents
    Peng, Zhihua
    Wang, Yilei
    Yu, Zhi
    Wu, Hao
    Fu, Shanshan
    Song, Linhua
    Jiang, Cuiyu
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (09) : 2048 - 2053
  • [43] Transition metal-catalyzed α-alkylation of amines by C(sp3)-H bond activation
    Gonnard, Laurine
    Guerinot, Amandine
    Cossy, Janine
    TETRAHEDRON, 2019, 75 (02) : 145 - 163
  • [44] Oxidative C(sp3)-H amidation of tertiary arylamines with nitriles
    Lin, Binzhou
    Shi, Shanshan
    Cui, Yiqun
    Liu, Yupei
    Tang, Guo
    Zhao, Yufen
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (19): : 2860 - 2863
  • [45] Dithiane-directed Rh(III)-catalyzed amidation of unactivated C(sp3)-H bonds
    Shi, Heyao
    Dixon, Darren J.
    CHEMICAL SCIENCE, 2019, 10 (13) : 3733 - 3737
  • [46] Thioamide-Directed Cobalt(III)-Catalyzed Selective Amidation of C(sp3)-H Bonds
    Tan, Peng Wen
    Mak, Adrian M.
    Sullivan, Michael B.
    Dixon, Darren J.
    Seayad, Jayasree
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (52) : 16550 - 16554
  • [47] Palladium-Catalyzed Intermolecular C(sp3)-H Amidation
    Iglesias, Alvaro
    Alvarez, Rosana
    de Lera, Angel R.
    Muniz, Kilian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (09) : 2225 - 2228
  • [48] sp3 C-H Arylation and Alkylation Enabled by the Synergy of Triplet Excited Ketones and Nickel Catalysts
    Shen, Yangyang
    Gu, Yiting
    Martin, Ruben
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (38) : 12200 - 12209
  • [49] Benzaldehyde- and Nickel-Catalyzed Photoredox C(sp3)-H Alkylation/Arylation with Amides and Thioethers
    Si, Xiaojia
    Zhang, Lumin
    Hashmi, A. Stephen K.
    ORGANIC LETTERS, 2019, 21 (16) : 6329 - 6332
  • [50] ORGN 427-Arylation and alkylation of sp3 C-H bonds in carboxylic acid derivatives
    Shabashov, Dmitry
    Daugulis, Olafs
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
12345