Stereoselective synthesis of vinyl sulfones by the Stille coupling of (E)-α-stannylvinyl sulfones with aryl halides

被引:4
|
作者
Hu, Ronghua [1 ,2 ]
Yu, Yan [1 ]
Cai, Mingzhong [1 ]
机构
[1] Jiangxi Normal Univ, Dept Chem, Nanchang 330022, Peoples R China
[2] Jinggangshan Univ, Dept Chem, Jian 343009, Jiangxi, Peoples R China
关键词
acetylenic sulfone; hydrostannylation; (E)-alpha-stannylvinyl sulfone; Stille coupling; (Z)-1,2-disubstituted vinyl sulfone;
D O I
10.3184/030823408X360319
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Palladium-catalysed hydrostannylation of acetylenic sulfones (R-C C-SO2Ar) in benzene at room temperature gives stereoselectively (E)-alpha-stannylvinyl sulfones in good to high yields. (E)-alpha-Stannylvinyl sulfones are difunctional group reagents which undergo Stifle coupling reaction with aryl halides in the presence of Pd(PPh3)(4) and Cul co-catalyst to afford stereoselectively (Z)-1,2-disubstituted vinyl sulfones in good yields.
引用
收藏
页码:592 / 594
页数:3
相关论文
共 50 条
  • [21] Zn/CuI-mediated coupling of alkyl halides with vinyl sulfones, vinyl sulfonates, and vinyl sulfonamides
    Zhao, MM
    Qu, CX
    Lynch, JE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17): : 6944 - 6947
  • [22] Stereoselective synthesis of vinyl sulfones by carbomagnesiation of acetylenic sulfone in the presence of CuCN
    Xie, MH
    Liu, L
    Wang, JL
    Wang, SW
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (17) : 4058 - 4062
  • [23] ARYL VINYL SULFONES AS THIOL PROTECTIVE GROUP
    KUROKI, Y
    LETT, R
    [J]. TETRAHEDRON LETTERS, 1984, 25 (02) : 197 - 200
  • [24] ON SYNTHESIS OF ARYL METHOXYMETHYL SULFONES
    MULDER, RJ
    VANLEUSE.AM
    STRATING, J
    [J]. TETRAHEDRON LETTERS, 1967, (32) : 3061 - &
  • [25] AN IMPROVED SYNTHESIS OF ARYL SULFONES
    SIPE, HJ
    CLARY, DW
    WHITE, SB
    [J]. SYNTHESIS-STUTTGART, 1984, (03): : 283 - 284
  • [26] NEW SYNTHESIS OF VINYL SULFONES
    BOLL, W
    [J]. LIEBIGS ANNALEN DER CHEMIE, 1979, (11): : 1665 - 1674
  • [27] Copper-Catalyzed Radical Reaction of N-Tosylhydrazones: Stereoselective Synthesis of (E)-Vinyl Sulfones
    Mao, Shuai
    Gao, Ya-Ru
    Zhu, Xue-Qing
    Guo, Dong-Dong
    Wang, Yong-Qiang
    [J]. ORGANIC LETTERS, 2015, 17 (07) : 1692 - 1695
  • [28] Zn-CuI-mediated coupling of alkyl halides with vinyl sulfones, vinyl sulfonates and vinyl sulfonamides.
    Zhao, MM
    Qu, CX
    Lynch, JE
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U390 - U390
  • [29] Controlled Synthesis of β-Keto Sulfones and Vinyl Sulfones under Electrochemical Oxidation
    Fang, Yang
    Xu, Dongping
    Yu, Yingliang
    Tang, Rumeng
    Dai, Shuaishuai
    Wang, Zhenghua
    Zhang, Wu
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (13)
  • [30] STEREOSELECTIVE PREPARATION OF VINYL SULFONES BY PROTODESILYLATION OF ALLYL SILANES
    FUNK, RL
    UMSTEADDAGGETT, J
    BRUMMOND, KM
    [J]. TETRAHEDRON LETTERS, 1993, 34 (18) : 2867 - 2870