Three-Component Coupling Reaction Triggered by Insertion of Arynes into the S=O Bond of DMSO

被引:147
|
作者
Liu, Feng-Lei [1 ]
Chen, Jia-Rong [1 ]
Zou, You-Quan [1 ]
Wei, Qiang [1 ]
Xiao, Wen-Jing [1 ,2 ]
机构
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 30072, Peoples R China
基金
美国国家科学基金会;
关键词
MULTICOMPONENT REACTIONS; STRAIGHTFORWARD SYNTHESIS; VINYLOGOUS AMIDES; N-HETEROAROMATICS; TERMINAL ALKYNES; QUINONE METHIDES; ACCESS; ISOCYANIDES; CHEMISTRY; HETEROANNULATION;
D O I
10.1021/ol501638x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unprecedented three-component coupling reaction of arynes, alpha-bromo carbonyl compounds, and DMSO triggered by insertion of arynes into the S=O bond of DMSO has been developed. The reaction can generate a wide range of multisubstituted aryl methyl thioethers in good yields, wherein DMSO serves as both methylthiolation reagent and oxygen source.
引用
收藏
页码:3768 / 3771
页数:4
相关论文
共 50 条
  • [1] Arynes in a three-component coupling reaction: Straightforward synthesis of benzoannulated iminofurans
    Yoshida, H
    Fukushima, H
    Ohshita, J
    Kunai, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) : 3935 - 3938
  • [2] Three-Component Coupling of Arynes and Organic Bromides
    Yoshida, Hiroto
    Asatsu, Yuji
    Mimura, Yasuhiro
    Ito, Yu
    Ohshita, Joji
    Takaki, Ken
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (41) : 9676 - 9679
  • [3] Three-component coupling of arynes, aminosilanes, and aldehydes
    Yoshida, Hiroto
    Morishita, Takami
    Fukushima, Hiroyuki
    Ohshita, Joji
    Kunai, Atsutaka
    ORGANIC LETTERS, 2007, 9 (17) : 3367 - 3370
  • [4] A Multicomponent Coupling Reaction Induced by Insertion of Arynes into the C=O Bond of Formamide
    Yoshioka, Eito
    Kohtani, Shigeru
    Miyabe, Hideto
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (29) : 6638 - 6642
  • [5] Three-Component Aminoselenation of Arynes
    Gaykar, Rahul N.
    Guin, Avishek
    Bhattacharjee, Subrata
    Biju, Akkattu T.
    ORGANIC LETTERS, 2019, 21 (23) : 9613 - 9617
  • [6] Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins
    Yoshioka, Eito
    Kohtani, Shigeru
    Miyabe, Hideto
    MOLECULES, 2014, 19 (01) : 863 - 880
  • [7] Synthetic Strategy for Aryl(alkynyl)phosphinates by a Three-Component Coupling Reaction Involving Arynes, Phosphites, and Alkynes
    Ji, Su Hyun
    Kim, Soomin
    Nam, Ghilsoo
    Lee, Duck-Hyung
    Han, Seo-Jung
    ORGANIC LETTERS, 2022, 24 (45) : 8295 - 8299
  • [8] A NOVEL THREE-COMPONENT COUPLING REACTION OF ARYNES, ISOCYANIDES, AND CYANOFORMATES: A STRAIGHTFORWARD ACCESS TO CYANO-SUBSTITUTED IMINOISOBENZOFURANS
    Li, Jing
    Noyori, Shintaro
    Iwasaki, Masayuki
    Nakajima, Kiyohiko
    Nishihara, Yasushi
    HETEROCYCLES, 2012, 86 (02) : 933 - 940
  • [9] Access to Sulfocoumarins by Three-Component Reaction of β-Keto Sulfonyl Fluorides, Arynes, and DMF
    Huang, Yuan
    Zhao, Xueyan
    Chen, Dengfeng
    Zheng, Yu
    Luo, Jinyue
    Huang, Shenlin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (27)
  • [10] Three-component reaction of small-ring cyclic amines with arynes and acetonitrile
    Stephens, David
    Zhang, Yu
    Cormier, Mathew
    Chavez, Gabriel
    Arman, Hadi
    Larionov, Oleg V.
    CHEMICAL COMMUNICATIONS, 2013, 49 (58) : 6558 - 6560