A general and practical sulfonylation of benzylic ammonium salts with sulfonyl hydrazides for the synthesis of sulfones

被引:12
|
作者
Zhu, Haibo [1 ]
Zhang, Yingying [1 ]
Liu, Yishuai [1 ]
Yang, Liu [1 ]
Xie, Zongbo [1 ]
Jiang, Guofang [1 ]
Le, Zhang-Gao [1 ]
机构
[1] East China Univ Technol, Sch Chem Biol & Mat Sci, Nanchang 330013, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
Sulfones; C-N cleavage; C-S formation; Transition-metal-free; UNSYMMETRICAL DIARYL SULFONES; CATALYZED ELECTROPHILIC AMINATION; S BOND FORMATION; BORONIC ACIDS; ARYL HALIDES; STEREOSELECTIVE-SYNTHESIS; COUPLING REACTION; CROSS-COUPLINGS; SULFUR-DIOXIDE; ALKYL-HALIDES;
D O I
10.1016/j.tetlet.2020.151975
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and efficient approach adopting transition-metal-free cross-coupling of sulfonyl hydrazides with benzyl ammonium salts has been developed to synthesize benzyl sulfones using Cs2CO3 as base under mild conditions. The protocol employs stable and easy to handle coupling partners, and is endowed with good substrate compatibility, leading to functional benzyl sulfones in good yields. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数:5
相关论文
共 40 条
  • [31] I2-mediated sulfonylation and Na2SO3-mediated deacylation: a general protocol for the synthesis of β-keto sulfones and β-dicarbonyl sulfones
    Gao, Wen-Chao
    Zhao, Jin-Jin
    Hu, Fei
    Chang, Hong-Hong
    Li, Xing
    Wei, Wen-Long
    RSC ADVANCES, 2015, 5 (32): : 25222 - 25228
  • [32] One-pot Synthesis of Pyrazolone Sulfones by Iodine-catalyzed Sulfenylation of Pyrazolones with Aryl Sulfonyl Hydrazides Followed by Oxidation in Water
    Zhao, Xia
    Lu, Xiaoyu
    Zhang, Lipeng
    Li, Tianjiao
    Lu, Kui
    CURRENT ORGANIC SYNTHESIS, 2018, 15 (03) : 380 - 387
  • [33] Oxidant-free C-H sulfonylation of enamides: Electrochemical synthesis of p-amidovinyl and carbonyl sulfones from sulfonyl hydrazide and enamides
    Qi, Liang
    Xiao, Linxia
    Chen, Xi
    Zhang, Ziyi
    Shi, Qin
    Chen, Jinkang
    TETRAHEDRON LETTERS, 2022, 88
  • [34] Transition-Metal Free C(sp3)-H Sulfonylation for the Synthesis of 2-Sulfolmethyl Quinolines from 2-Methylquinolines and Sulfonyl Hydrazides
    Li, Qian
    Zhu, Haibo
    Yang, Liu
    Meng, Jia
    Xie, Zongbo
    Le, Zhang-Gao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (12)
  • [35] A general synthesis of quinone ammonium salts: Bifunctional materials for charge-transfer studies
    Wiedenfeld, David
    Glass, David R.
    Minton, Mark
    Nesterov, Vladimir
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [36] Pd-Catalyzed Annulation of β-Iodovinyl Sulfones with 2-Halophenols: A General Route for the Synthesis of 3-Sulfonyl Benzofuran Derivatives
    Reddy, Raju Jannapu
    Kumar, Jangam Jagadesh
    Kumari, Arram Haritha
    Krishna, Gamidi Rama
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (06) : 1317 - 1322
  • [37] Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions
    Miyamoto, Naoki
    Koseki, Daichi
    Sumida, Kohei
    Elboray, Elghareeb E.
    Takenaga, Naoko
    Kumar, Ravi
    Dohi, Toshifumi
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 1020 - 1028
  • [38] Directed synthesis and immunoactive properties of (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanyl(sulfonyl)alkanecarboxylic acids
    Mirskova, A. N.
    Levkovskaya, G. G.
    Kolesnikova, O. P.
    Perminova, O. M.
    Rudyakova, E. V.
    Adamovich, S. N.
    RUSSIAN CHEMICAL BULLETIN, 2010, 59 (12) : 2236 - 2246
  • [39] Directed synthesis and immunoactive properties of (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanyl(sulfonyl)alkanecarboxylic acids
    A. N. Mirskova
    G. G. Levkovskaya
    O. P. Kolesnikova
    O. M. Perminova
    E. V. Rudyakova
    S. N. Adamovich
    Russian Chemical Bulletin, 2010, 59 : 2236 - 2246
  • [40] SYNTHESIS OF ALPHA,BETA-UNSATURATED SULFIDES, SULFOXIDES, AND SULFONES BY HORNER-WITTIG REACTION IN 2-PHASE SYSTEM CATALYZED BY QUATERNARY AMMONIUM-SALTS AND CROWN ETHERS
    MIKOLAJCZYK, M
    GRZEJSZCZAK, S
    MIDURA, W
    ZATORSKI, A
    SYNTHESIS-STUTTGART, 1975, (04): : 278 - 280