I2/TBHP-Promoted Approach to α-Keto Esters from Trifluoromethyl β-Diketones and Alcohols via C-C Bond Cleavage

被引：6
|
作者：
Shao, Tongle [1 ,2 ]
Fang, Xiang [1 ,2 ]
Zhou, Jun [1 ,2 ]
Jin, Chen [1 ,2 ]
Yang, Xueyan [1 ,2 ]
Wu, Fanhong [3 ]
机构：
[1] East China Univ Sci & Technol, Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China
[3] Shanghai Inst Technol, Sch Chem & Environm Engn, 120 Caobao Rd, Shanghai 200235, Peoples R China
来源：
SYNLETT | 2017年 / 28卷 / 15期
基金：
中国国家自然科学基金;
关键词：
trifluoromethyl beta-diketones; alpha-keto esters; C-C bond cleavage; C-O coupling; alcohols; ENANTIOSELECTIVE OXIDATIVE CYCLOETHERIFICATION; CATALYZED DOUBLE CARBONYLATION; FLUORINATED GEM-DIOLS; ONE-POT SYNTHESIS; METAL-FREE; H FUNCTIONALIZATION; CARBOXYLIC-ACIDS; FACILE SYNTHESIS; KETOESTERS; ESTERIFICATION;
D O I：
10.1055/s-0036-1588833
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal-free oxidative coupling reaction of trifluoromethyl beta-diketones with alcohols for the synthesis of alpha-keto esters in good to excellent yields has been developed. Preliminary mechanistic studies suggest that an I-2/TBHP promoted sequential iodination, C-C bond cleavage, C-O bond formation and oxidation pathway is involved in this reaction.
引用
收藏
页码：2018 / 2023
页数：6
相关论文
共 50 条
  • [1] A novel and metal-free approach towards α-ketoamides using a TBHP/I2-promoted tandem reaction of amines with β-diketones via C-C bond cleavage
    Zhang, Xiaobin
    Wang, Min
    Zhang, Yicheng
    Wang, Lei
    RSC ADVANCES, 2013, 3 (05): : 1311 - 1316
  • [2] The direct amidation of α-diketones with amines via TBHP-promoted oxidative cleavage of C(sp2)-C(sp2) bonds
    Zhao, Qiong
    Li, Hongji
    Wang, Lei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (39) : 6772 - 6779
  • [3] 1,4-Refunctionalization of β-diketones to γ-keto nitriles via C-C single bond cleavage
    Wu, Qi
    Li, Yabo
    Wang, Chenyang
    Zhang, Jianye
    Huang, Mengmeng
    Kim, Jung Keun
    Wu, Yangjie
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (16): : 2496 - 2500
  • [4] Ag(I)-Catalyzed Addition of Cyclopropenones and Alcohols via C-C Bond Cleavage
    Zhang Shulin
    Zhang Zhou
    Sun Meng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (07) : 2233 - 2240
  • [5] Amidation of β-Keto Sulfonyl Fluorides via C-C Bond Cleavage
    Liang, Hui
    Liu, Qian
    Zhao, Xueyan
    He, Tianyu
    Luo, Jinyue
    Huang, Shenlin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (27)
  • [6] Rhenium-Promoted C-C Bond-Cleavage Reactions of Internal Propargyl Alcohols
    Lee, Kui Fun
    Bai, Wei
    Sung, Herman H. Y.
    Williams, Ian D.
    Lin, Zhenyang
    Jia, Guochen
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (39) : 9760 - 9764
  • [7] Synthesis of Biaryls via Benzylic C-C Bond Cleavage of Styrenes and Benzyl Alcohols
    Kumar, Arvind
    Shah, Bhahwal All
    ORGANIC LETTERS, 2015, 17 (21) : 5232 - 5235
  • [8] Radical-Promoted C-C Bond Cleavage: A Deconstructive Approach for Selective Functionalization
    Morcillo, Sara P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (40) : 14044 - 14054
  • [9] AIBN-promoted amidation of anilines with 1, 3-diketones via oxidative cleavage of C-C bond under aerobic conditions
    Rao, Sadu Nageswara
    Mohan, Darapaneni Chandra
    Adimurthy, Subbarayappa
    TETRAHEDRON, 2016, 72 (32) : 4889 - 4894
  • [10] COPPER(I) PROMOTED C-C BOND FORMING REACTIONS - DIRECT ACTIVATION OF ALLYL ALCOHOLS
    BARUAH, JB
    SAMUELSON, AG
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 361 (03) : C57 - C60
12345