Coupling of Sulfoxonium Ylides with Arynes: A Direct Synthesis of Pro-Chiral Aryl Ketosulfoxonium Ylides and Its Application in the Preparation of α-Aryl Ketones

被引：71
作者：
Talero, Alexander Garay [1 ]
Martins, Bruna Simoes [1 ]
Burtoloso, Antonio C. B. [1 ]
机构：
[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP, Brazil
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 22期
基金：
巴西圣保罗研究基金会;
关键词：
DIAZO-CARBONYL-COMPOUNDS; H INSERTION REACTIONS; SULFUR YLIDES; FORMAL SYNTHESIS; SULFONIUM; ARYLATION; BONDS; FUNCTIONALIZATION; CYCLOPROPANATION; DECOMPOSITION;
D O I：
10.1021/acs.orglett.8b03126
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general, mild, and versatile synthesis of the challenging alpha-aryl-beta-ketosulfoxonium ylides has been developed for the first time, substituting traditional methods starting from diazo compounds. The arylation of easily accessible beta-ketosulfoxonium ylides using aryne chemistry allowed the preparation of a large scope of the pro-chiral ylides in very good yields (40 examples; up to 85%). As applications, these ylides were smoothly converted into alpha-aryl ketones after desulfurization in good yields (up to 98%) as well as in other important derivatives.
引用
收藏
页码：7206 / 7211
页数：6
相关论文
共 78 条
  • [11] α-Monoarylation and tandem arylation-insertion of malonates with arynes
    Chen, Qian
    Zhang, Changyuan
    Chen, Lili
    Wen, Chunxiao
    Du, Zhiyun
    Chen, Huixiong
    Zhang, Kun
    [J]. TETRAHEDRON LETTERS, 2015, 56 (16) : 2094 - 2097
  • [12] DIMETHYLSULFOXONIUM METHYLIDE
    COREY, EJ
    CHAYKOVSKY, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) : 867 - &
  • [13] DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS
    COREY, EJ
    CHAYKOVSKY, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) : 1353 - +
  • [14] FORMATION + PHOTOCHEMICAL REARRANGEMENT OF BETA]-KETOSULFOXONIUM YLIDES
    COREY, EJ
    CHAYKOVSKY, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (08) : 1640 - &
  • [15] Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of β-Keto Thioethers
    Dias, Rafael M. P.
    Burtoloso, Antonio C. B.
    [J]. ORGANIC LETTERS, 2016, 18 (12) : 3034 - 3037
  • [16] DOST F, 1970, TETRAHEDRON LETT, P5091
  • [17] DOYLE MP, 1995, COMPREHENSIVE ORGANO, V12, P421
  • [18] Modern Organic Synthesis with α-Diazocarbonyl Compounds
    Ford, Alan
    Miel, Hugues
    Ring, Aoife
    Slattery, Catherine N.
    Maguire, Anita R.
    McKervey, M. Anthony
    [J]. CHEMICAL REVIEWS, 2015, 115 (18) : 9981 - 10080
  • [19] Highly active and selective catalysts for the formation of α-aryl ketones
    Fox, JM
    Huang, XH
    Chieffi, A
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) : 1360 - 1370
  • [20] α,α-Alkylation-Halogenation and Dihalogenation of Sulfoxonium Ylides. A Direct Preparation of Geminal Difunctionalized Ketones
    Gallo, Rafael D. C.
    Ahmad, Anees
    Metzker, Gustavo
    Burtoloso, Antonio C. B.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (67) : 16980 - 16984
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