Rapid and efficient deoxygenation of sulfoxides to sulfides with tantalum(V) chloride/sodium iodide system

被引:7
|
作者
Yoo, Byung Woo [1 ]
Park, Jeeyeon [1 ]
Shin, Hyo Jong [1 ]
Yoon, Cheol Min [1 ]
机构
[1] Korea Univ, Dept Adv Mat Chem, 2511 Sejong Ro, Sejong 339700, South Korea
关键词
Deoxygenation; sulfoxide; sulfide; tantalum(V) chloride; sodium iodide; REDUCTION; SELENOXIDES; SULFONES; FACILE; MILD;
D O I
10.1080/17415993.2017.1337770
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
TaCl5/NaI system converts a wide range of sulfoxides to the corresponding sulfides in high yields with short reaction times, under mild conditions. It is worth mentioning that this protocol is chemoselective and tolerates various functional groups (such as -Br, -Cl, -OCH3, -CHO, and -NO2) and double bond. [GRAPHICS] .
引用
收藏
页码:597 / 603
页数:7
相关论文
共 50 条
  • [21] AN EFFICIENT DEOXYGENATION OF 1-ALKENYL OR ALKYL PHENYL SULFOXIDES TO THE CORRESPONDING SULFIDES MEDIATED BY MAGNESIUM IN ALCOHOL
    LEE, GH
    CHOI, EB
    LEE, E
    PAK, CS
    TETRAHEDRON LETTERS, 1994, 35 (14) : 2195 - 2196
  • [22] Selective synthesis of sulfoxides and sulfones by tantalum(V) catalyzed oxidation of sulfides with 30% hydrogen peroxide
    Kirihara, Masayuki
    Yamamoto, Junya
    Noguchi, Takuya
    Hirai, Yoshiro
    TETRAHEDRON LETTERS, 2009, 50 (11) : 1180 - 1183
  • [23] Mild and efficient deoxygenation of sulfoxides with MoCl5/indium system
    Yoo, Byung Woo
    Song, Min Suk
    Park, Min Chol
    SYNTHETIC COMMUNICATIONS, 2007, 37 (18) : 3089 - 3093
  • [24] SYNTHETIC METHODS AND REACTIONS .45. DEOXYGENATION OF SULFOXIDES WITH TRIPHENYLPHOSPHINE-IODINE-SODIUM IODIDE REAGENT
    OLAH, GA
    BALARAMGUPTA, BG
    NARANG, SC
    SYNTHESIS-STUTTGART, 1978, (02): : 137 - 138
  • [25] MILD REDUCTIONS OF SULFOXIDES WITH TRIFLUOROACETIC ANHYDRIDE SODIUM IODIDE SYSTEM
    DRABOWICZ, J
    OAE, S
    SYNTHESIS-STUTTGART, 1977, (06): : 404 - 405
  • [26] Selective and Efficient Deoxygenation of Sulfoxides with NbCl5/Indium System
    Yoo, Byung Woo
    Kim, Hyung Min
    Kim, Duckil
    SYNTHETIC COMMUNICATIONS, 2013, 43 (15) : 2057 - 2061
  • [27] EXCEPTIONALLY RAPID AND SELECTIVE DEOXYGENATION OF ALIPHATIC SULFOXIDES TO SULFIDES UNDER MILD CONDITIONS WITH A NEW REDUCING AGENT, DICHLOROBORANE
    BROWN, HC
    RAVINDRAN, N
    SYNTHESIS-STUTTGART, 1973, (01): : 42 - 44
  • [28] Deoxygenation of tertiary and secondary alcohols with sodium borohydride, trimethylsilyl chloride, and potassium iodide in acetonitrile
    Kato, Yuichi
    Inoue, Tomoka
    Furuyama, Yuuki
    Ohgane, Kenji
    Sadaie, Mahito
    Kuramochi, Kouji
    TETRAHEDRON LETTERS, 2021, 86
  • [29] Efficient Oxidation of Sulfides to the Sulfoxides Using Zirconium (IV) Chloride, Sodium Nitrite and Catalytic Amounts of Bromide Ion as a Novel Oxidizing Media
    Ghorbani-Choghamarani, Arash
    Goudarziafshar, Hamid
    Nikoorazm, Mohsen
    Yousefi, Somaieh
    LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (04) : 335 - 339
  • [30] Rapid and mild deoxygenation of sulfoxides with MoCl5/gallium system under ultrasonication
    Department of Advanced Materials Chemistry, Korea University, Jochiwon, Chungnam 339-700, Korea, Republic of
    Bull. Korean Chem. Soc., 2009, 9 (1927-1928):