NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions

被引:13
|
作者
Zhang, Guofu [1 ]
Fan, Qiankun [1 ]
Wang, Huimin [1 ]
Zhao, Yiyong [2 ]
Ding, Chengrong [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Peoples R China
[2] Zhejiang Ecol Environm Low Carbon Dev Ctr, Hangzhou 310012, Peoples R China
基金
中国国家自然科学基金;
关键词
sulfonyl hydrazides; alcohols; sulfinic esters; transition-metal-free; radical pathway; ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ARENESULFONYL CHLORIDES; EFFICIENT; ALKENES;
D O I
10.1002/adsc.202001202
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We have developed a protocol for the NaHSO3-promoted esterification of sulfonyl hydrazides with alcohols for the synthesis of sulfinic esters. Various sulfonyl hydrazides could be converted to the corresponding sulfinic esters in good to high yields. The merits of this protocol include mild transition-metal-free reaction conditions, an inexpensive and available reagent, and operational simplicity. Controlled experiments reveal that this transformation probably undergoes via a radical pathway.
引用
收藏
页码:833 / 837
页数:5
相关论文
共 50 条
  • [21] Recent Advance on the Synthesis of 3,3'-Bisindolylmethane Derivatives under Transition-Metal-Free Catalytic Conditions
    Zhang, Zhenguo
    Liu, Xiaoxiao
    Zong, Xinlong
    Yuan, Yalin
    Liu, Shuanglei
    Zhang, Ting
    Wu, Zishang
    Yang, Jingying
    Jia, Zhenhua
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (01) : 52 - 64
  • [22] Transition-Metal-Free Synthesis of Quinoxalines from o-Phenylenediamines and Arylacetaldehydes under Basic Conditions
    Song, Jinli
    Li, Xiaolong
    Chen, Yongxin
    Zhao, Mingming
    Dou, Yani
    Chen, Baohua
    SYNLETT, 2012, (16) : 2416 - 2420
  • [23] Synthesis of 1,4-benzoxazine derivatives from α-aminocarbonyls under transition-metal-free conditions
    Hao, Liqiang
    Wu, Gaorong
    Wang, Yangyang
    Xu, Xiaobo
    Ji, Yafei
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (20) : 9527 - 9531
  • [24] Transition-Metal-Free Synthesis of Benzimidazoles Mediated by KOH/DMSO
    Baars, Hannah
    Beyer, Astrid
    Kohlhepp, Stefanie V.
    Bolm, Carsten
    ORGANIC LETTERS, 2014, 16 (02) : 536 - 539
  • [25] Three-Component Synthesis of Dibenzoxazepinamines and Dibenzothiazepinamines under Transition-Metal-Free Conditions
    Fang, Fang
    Jiang, Shuxin
    Lei, Hanwen
    Chen, Shanping
    Deng, Guo-Jun
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 15658 - 15664
  • [26] Direct Amidation of Alcohols with N-Substituted Formamides under Transition-Metal-Free Conditions
    Xu, Kun
    Hu, Yanbin
    Zhang, Sheng
    Zha, Zhenggen
    Wang, Zhiyong
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (32) : 9793 - 9797
  • [27] One-Pot Synthesis of Thiocarbamide Esters: Construction of C-S Bonds under Transition-Metal-Free Conditions
    Deng, Shi-Hao
    Yu, Jun-Xia
    Xiao, Hua-Qing
    Dong, Zhi-Bing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (46)
  • [28] Transition-metal-free NaI-mediated reaction of aryl sulfonyl chloride with alkynes: Synthesis of (E)-β-iodovinyl sulfones
    Chen, Dan
    Lin, Li
    Peng, Xiaoyan
    Yu, Xinyi
    Yang, Zhonglie
    Liu, Yutong
    Zhang, Xiaobin
    Li, Jiahong
    Jiang, Hezhong
    TETRAHEDRON LETTERS, 2021, 75
  • [29] Transition-Metal-Free Synthesis of Phenanthridinones from Biaryl-2-oxamic Acid under Radical Conditions
    Yuan, Ming
    Chen, Li
    Wang, Junwei
    Chen, Shenjie
    Wang, Kongchao
    Xue, Yongbo
    Yao, Guangmin
    Luo, Zengwei
    Zhang, Yonghui
    ORGANIC LETTERS, 2015, 17 (02) : 346 - 349
  • [30] Synthesis of Multiarmed Thienylene-Tetrafluorophenylene Alternating Copolymers under Transition-Metal-Free Conditions
    Sanji, Takanobu
    Kakinuma, Junko
    Iyoda, Tomokazu
    MACROMOLECULES, 2016, 49 (18) : 6761 - 6767