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
  • [21] A general method for preparation of metal carbenes via solution- and polymer-based approaches
    Gandelman, M
    Naing, KM
    Rybtchinski, B
    Poverenov, E
    Ben-David, Y
    Ashkenazi, N
    Gauvin, RM
    Milstein, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) : 15265 - 15272
  • [22] Catalytic X-H insertion reactions based on carbenoids
    Gillingham, Dennis
    Fei, Na
    [J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) : 4918 - 4931
  • [23] Rhodium(III)-Catalyzed imidoyl C-H Activation for Annulations to Azolopyrimidines
    Halskov, Kim Soholm
    Witten, Michael R.
    Hoang, Gia L.
    Mercado, Brandon Q.
    Ellman, Jonathan A.
    [J]. ORGANIC LETTERS, 2018, 20 (08) : 2464 - 2467
  • [24] Developments of Corey-Chaykovsky in Organic Reactions and Total Synthesis of Natural Products
    Heravi, Majid M.
    Asadi, Shima
    Nazari, Niousha
    Lashkariani, Boshra Malekzadeh
    [J]. CURRENT ORGANIC SYNTHESIS, 2016, 13 (03) : 308 - 333
  • [25] Rhodium(III)-catalyzed C-H functionalization of C-alkenyl azoles with sulfoxonium ylides for the synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles
    Hoang, Gia L.
    Ellman, Jonathan A.
    [J]. TETRAHEDRON, 2018, 74 (26) : 3318 - 3324
  • [26] Construction of (Dihydro)naphtho[1,8-bc]pyrans via Rh(III)-Catalyzed Twofold C-H Activation of Benzoylacetonitriles
    Hu, Panjie
    Zhang, Ying
    Xu, Youwei
    Yang, Shuang
    Liu, Bingxian
    Li, Xingwei
    [J]. ORGANIC LETTERS, 2018, 20 (08) : 2160 - 2163
  • [27] Practical and Highly Selective Sulfur Ylide Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive, Readily Available Chiral Sulfide. Applications to the Synthesis of Quinine and Quinidine
    Illa, Ona
    Arshad, Muhammad
    Ros, Abel
    McGarrigle, Eoghan M.
    Aggarwal, Varinder K.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) : 1828 - +
  • [28] Metal-Catalyzed α-Arylation of Carbonyl and Related Molecules: Novel Trends in C-C Bond Formation by C-H Bond Functionalization
    Johansson, Carin C. C.
    Colacot, Thomas J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (04) : 676 - 707
  • [29] Simple, highly active palladium catalysts for ketone and malonate arylation: Dissecting the importance of chelation and steric hindrance
    Kawatsura, M
    Hartwig, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (07) : 1473 - 1478
  • [30] Kessar S.V., 1991, Comp. Org. Synth, V4, P483
12345678