Facile C-S Bond Cleavage of Aryl Sulfoxides Promoted by Bronsted Acid

被引:1
|
作者
Brutiu, Bogdan R. [1 ]
Klose, Immo [1 ]
Maulide, Nuno [1 ]
机构
[1] Univ Vienna, Inst Organ Chem, Wahringer Str 38, A-1090 Vienna, Austria
基金
欧盟地平线“2020”;
关键词
sulfoxides; protodesulfination; deprotection; acid;
D O I
10.1055/s-0040-1707109
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the Bronsted acid promoted desulfination of aryl sulfoxides is presented. In the presence of a thiol, electron-rich sulfoxides undergo C-S bond cleavage to give the corresponding protodesulfinated arenes and disulfides.
引用
收藏
页码:488 / 490
页数:3
相关论文
共 50 条
  • [1] Unusual nickel-mediated C-S cleavage of alkyl and aryl sulfoxides
    Schaub, Thomas
    Backes, Marc
    Radius, Udo
    [J]. CHEMICAL COMMUNICATIONS, 2007, (20) : 2037 - 2039
  • [2] Photosensitized Oxidation of Aryl Benzyl Sulfoxides. Evidence for Nucleophilic Assistance to the C-S Bond Cleavage of Aryl Benzyl Sulfoxide Radical Cations
    Del Giacco, Tiziana
    Lanzalunga, Osvaldo
    Lapi, Andrea
    Mazzonna, Marco
    Mencarelli, Paolo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (04): : 2310 - 2318
  • [3] C-S bond cleavage in pyridylmethylthioether systems promoted by oxorhenium(V) ion
    Das, Biswajit
    Sarkar, Sandipan
    Zangrando, Ennio
    Chattopadhyay, Pabitra
    [J]. INORGANIC CHEMISTRY COMMUNICATIONS, 2009, 12 (11) : 1112 - 1115
  • [4] The mechanism of photochemical C-O or C-S bond cleavage in aryl(thio)ethers
    Pohlers, G
    Dreeskamp, H
    Grimme, S
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1996, 95 (01) : 41 - 49
  • [5] CLEAVAGE OF C-S BOND IN ALLYLIC ARYL SULFIDES PROMOTED BY RHODIUM HYDRIDE COMPLEX - REACTION-MECHANISMS OF ALLYL-SULFUR BOND FISSION
    OSAKADA, K
    MATSUMOTO, K
    YAMAMOTO, T
    YAMAMOTO, A
    [J]. ORGANOMETALLICS, 1985, 4 (05) : 857 - 862
  • [6] Transition-Metal-Free Aryl-Heteroatom Bond Formation via C-S Bond Cleavage
    Zhao, Jian-Nan
    Kayumov, Muzaffar
    Wang, Dong-Yu
    Zhang, Ao
    [J]. ORGANIC LETTERS, 2019, 21 (18) : 7303 - 7306
  • [7] Structural and Solvent Effects on the C-S Bond Cleavage in Aryl Triphenylmethyl Sulfide Radical Cations
    Del Giacco, Tiziana
    Lanzalunga, Osvaldo
    Mazzonna, Marco
    Mencarelli, Paolo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (04): : 1843 - 1852
  • [8] SINGLET OXYGEN OXIDATION OF ALKYL 4-NITROPHENYL SULFIDES AND SULFOXIDES - OXIDATIVE CLEAVAGE OF THE C-S BOND
    PASTO, DJ
    COTTARD, F
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 9 - ORGN
  • [9] Photoinduced C-S Bond Cleavage of Thioglycosides and Glycosylation
    Mao, Run-Ze
    Guo, Fan
    Xiong, De-Cai
    Li, Qin
    Duan, Jinyou
    Ye, Xin-Shan
    [J]. ORGANIC LETTERS, 2015, 17 (22) : 5606 - 5609
  • [10] CLEAVAGE OF C-S BOND DURING OXIDATION OF THIOL
    COLE, ER
    [J]. CHEMISTRY & INDUSTRY, 1957, (46) : 1511 - 1511