Efficient synthesis of β-substituted α-haloenones by rhodium(II) catalyzed and thermal reactions of iodonium ylides

被引:26
|
作者
Lee, YR [1 ]
Jung, YU [1 ]
机构
[1] Yeungnam Univ, Coll Engn, Sch Chem Engn & Technol, Kyongsan 712749, South Korea
关键词
D O I
10.1039/b111206f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium(II)-catalyzed and thermal reaction of iodonium ylides are described. Rhodium(II)-catalyzed reactions of iodonium ylides with benzyl halides and acid halides afforded alpha-chloro-alpha,beta-enones and alpha-bromo-alpha,beta-enones in good yields, whereas thermal reactions of iodonium ylides in a solvent such as benzene afforded alpha-iodo-alpha,beta-enones in good yields.
引用
收藏
页码:1309 / 1313
页数:5
相关论文
共 50 条
  • [21] Hetaryl-Substituted Phosphonium-Iodonium Ylides in Synthesis of Heterocycles
    Matveeva, Elena D.
    Podrugina, Tatyana A.
    Taranova, Marina A.
    Ivanova, Anastasiya M.
    Gleiter, Rolf
    Zefirov, Nikolay S.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (13): : 5770 - 5774
  • [22] A simple synthesis of fluoroalkyl substituted dihydrofurans by rhodium(II)-catalyzed 1,3-dipolar reactions
    Wang, YL
    Zhu, SZ
    TETRAHEDRON, 2001, 57 (16) : 3383 - 3387
  • [23] Regioselective cyclopropanation reactions using iodonium ylides: Synthesis of prostaglandin precursors
    Moriarty, RM
    May, EJ
    Guo, L
    Prakash, O
    TETRAHEDRON LETTERS, 1998, 39 (08) : 765 - 766
  • [24] Rhodium-Catalyzed Rearrangement Of S/Se-Ylides for the Synthesis. of Substituted Vinylogous Carbonates
    Chandra, Angula
    Reddy, Shekar
    Anbarasan, Pazhamalai
    ORGANIC LETTERS, 2019, 21 (24) : 9965 - 9969
  • [25] Rhodium-Catalyzed Synthesis of Sulfur Ylides via in Situ Generated lodonium Ylides
    Vaitla, Janakiram
    Hopmann, Kathrin H.
    Bayer, Annette
    ORGANIC LETTERS, 2017, 19 (24) : 6688 - 6691
  • [26] Rhodium-Catalyzed Carbene Transfer Reactions for Sigmatropic Rearrangement Reactions of Selenium Ylides
    Jana, Sripati
    Koenigs, Rene M.
    ORGANIC LETTERS, 2019, 21 (10) : 3653 - 3657
  • [27] Regioselective and Chemodivergent Synthesis of Azulenolactones and Azulenolactams from Rhodium(III)-Catalyzed Reactions of Azulenecarboxamides with Sulfoxonium Ylides
    Lee, Seung Cheol
    Son, Jeong-Yu
    Kim, Jin Young
    Eom, Hyeonsik
    Jang, Seong Bin
    Lee, Phil Ho
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) : 512 - 524
  • [28] Diversity synthesis using the complimentary reactivity of rhodium(II)- and palladium(II)-catalyzed reactions
    Ni, Aiwu
    France, Jessica E.
    Davies, Huw M. L.
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15): : 5594 - 5598
  • [29] Efficient synthesis of dihydrofurans and furans by rhodium(II)-catalyzed reactions of cyclic diazodicarbonyl compounds with allyl halides.
    Lee, YR
    Cho, BS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U188 - U188
  • [30] THERMAL GENERATION AND REACTIONS OF (BENZYLTHIO)-SUBSTITUTED AND (ARYLTHIO)-SUBSTITUTED NITRILE YLIDES
    WIPF, P
    PREWO, R
    BIERI, JH
    GERMAIN, G
    HEIMGARTNER, H
    HELVETICA CHIMICA ACTA, 1988, 71 (05) : 1177 - 1190