Cu-catalyzed aerobic oxidative synthesis of sulfonamides from sulfonyl hydrazides and amines

被引：12
作者：
Chung, Sohyun [1 ,2 ]
Kim, Jinho [1 ,2 ]
机构：
[1] Incheon Natl Univ, Dept Chem, 119 Acad Ro, Incheon 22012, South Korea
[2] Incheon Natl Univ, Res Inst Basic Sci, 119 Acad Ro, Incheon 22012, South Korea
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 11期
关键词：
Aerobic oxidation; Copper catalysis; Sulfonyl hydrazides; Sulfonamides; Organic synthesis; OXYGENATION; ANTICANCER; ALCOHOLS; CLEAVAGE; ACCESS;
D O I：
10.1016/j.tetlet.2019.02.016
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An environmentally friendly route for sulfonamides has been developed. The oxidative coupling of sulfonyl hydrazides and amines was catalyzed by CuBr2 to produce various sulfonamides with the water and nitrogen gas as byproducts. Preliminary experiments revealed that the sulfonyl radical is likely to be involved in the reaction mechanism. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：792 / 795
页数：4
相关论文
共 47 条
  • [1] Aerobic Copper-Catalyzed Organic Reactions
    Allen, Scott E.
    Walvoord, Ryan R.
    Padilla-Salinas, Rosaura
    Kozlowski, Marisa C.
    [J]. CHEMICAL REVIEWS, 2013, 113 (08) : 6234 - 6458
  • [2] KINETICS OF NITROXIDE RADICAL TRAPPING .2. STRUCTURAL EFFECTS
    BOWRY, VW
    INGOLD, KU
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) : 4992 - 4996
  • [3] Iodine-Catalyzed Oxidative Amination of Sodium Sulfinates: A Convenient Approach to the Synthesis of Sulfonamides under Mild Conditions
    Buathongjan, Chonchanok
    Beukeaw, Danupat
    Yotphan, Sirilata
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (07) : 1575 - 1582
  • [4] Neighbouring group assisted sulfonamide cleavage of sharpless aminols under acetonation conditions
    Chandrasekhar, S
    Mohapatra, S
    [J]. TETRAHEDRON LETTERS, 1998, 39 (07) : 695 - 698
  • [5] DEBOER TJ, 1954, ORG SYNTH, V34, P96
  • [6] Copper-Catalyzed Selective Aerobic Oxidative Cascade Reaction of Hydrazines, DABSO, and Amines for the Direct Synthesis of Sulfonamides
    Du, Bingnan
    Wang, Yang
    Sha, Wanxing
    Qian, Ping
    Mei, Haibo
    Han, Jianlin
    Pan, Yi
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (02) : 153 - 156
  • [7] Copper-Catalyzed Aerobic Oxidative Reaction of Sulfonyl Hydrazides with Alcohols: An Easy Access to Sulfinates
    Du, Bingnan
    Li, Zan
    Qian, Ping
    Han, Jianlin
    Pan, Yi
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (04) : 478 - 481
  • [8] Sulfinamides as Highly Effective Amine Protecting Groups and Their Use in the Conversion of Amino Alcohols into Morpholines
    Fritz, Sven P.
    Mumtaz, Amara
    Yar, Muhammad
    McGarrigle, Eoghan M.
    Aggarwal, Varinder K.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (17) : 3156 - 3164
  • [9] Building a Sulfonamide Library by Eco-Friendly Flow Synthesis
    Gioiello, Antimo
    Rosatelli, Emiliano
    Teofrasti, Michela
    Filipponi, Paolo
    Pellicciari, Roberto
    [J]. ACS COMBINATORIAL SCIENCE, 2013, 15 (05) : 235 - 239
  • [10] Green T.W., 1999, In Protecting Groups in Organic Synthsis
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