Bu4NI-catalyzed decarboxylative acyloxylation of an sp3 C-H bond adjacent to a heteroatom with α-oxocarboxylic acids

被引:73
|
作者
Zhang, Shuai
Guo, Li-Na [1 ]
Wang, Hua
Duan, Xin-Hua
机构
[1] Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Peoples R China
基金
中国国家自然科学基金;
关键词
KETO CARBOXYLIC-ACIDS; CROSS-COUPLING REACTION; DIRECT ARYLATION; BENZOIC-ACIDS; METAL-FREE; CATALYZED DIRECT; CINNAMIC-ACIDS; ARYL HALIDES; OXIDATION; ACTIVATION;
D O I
10.1039/c3ob40748a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel metal-free decarboxylative acyloxylation of an sp(3) C-H bond in formamides and ethers has been explored. A variety of N-acyloxymethylamides and a-acyloxy ethers could be easily synthesized by this method. Preliminary mechanistic studies have shown that the reaction proceeded via a radical process.
引用
收藏
页码:4308 / 4311
页数:4
相关论文
共 50 条
  • [41] Highly efficient copper-catalyzed nitro-mannich type reaction:: Cross-dehydrogenative-coupling between sp3 C-H bond and sp3 C-H bond
    Li, ZP
    Li, CJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3672 - 3673
  • [42] Transition-Metal-Catalyzed Acyloxylation: Activation of C(sp2)-H and C(sp3)-H Bonds
    Moghimi, Setareh
    Mahdavi, Mohammad
    Shafiee, Abbas
    Foroumadi, Alireza
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (20) : 3282 - 3299
  • [43] Preferential bond activation of sp3 C-H over sp2 C-H in α,β-unsaturated carboxylic acids by ruthenium complex
    Kanaya, S
    Komine, N
    Hirano, M
    Komiya, S
    CHEMISTRY LETTERS, 2001, (12) : 1284 - 1285
  • [44] Iron-Catalyzed N-Alkylation of Azoles via Cleavage of an sp3 C-H Bond Adjacent to a Nitrogen Atom
    Xia, Qinqin
    Chen, Wanzhi
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20): : 9366 - 9373
  • [45] Iron-catalyzed N-alkylation of azoles via cleavage of an sp3 C-H bond adjacent to a nitrogen atom
    Xia, Qinqin
    Chen, Wanzhi
    Journal of Organic Chemistry, 2012, 77 (20): : 9366 - 9373
  • [46] CuBr-catalyzed efficient alkynylation of sp3 C-H bonds adjacent to a nitrogen atom
    Li, ZP
    Li, CJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) : 11810 - 11811
  • [47] Carbonylation at sp3 C-H bonds adjacent to a nitrogen atom in alkylamines catalyzed by rhodium complexes
    Chatani, N
    Asaumi, T
    Ikeda, T
    Yorimitsu, S
    Ishii, Y
    Kakiuchi, F
    Murai, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) : 12882 - 12883
  • [48] CuBr-catalyzed efficient alkynylation of sp3 C-H bonds adjacent to a nitrogen atom
    1600, American Chemical Society, Columbus, United States (126):
  • [49] Pd(II)-Catalyzed Primary-C(sp3)-H Acyloxylation at Room Temperature
    Rit, Raja K.
    Yadav, M. Ramu
    Sahoo, Akhila K.
    ORGANIC LETTERS, 2012, 14 (14) : 3724 - 3727
  • [50] Palladium-Catalyzed Annulations via Sequential C-H Activations of C(sp2)-H/C(sp3)-H or C(sp3)-H/C(sp3)-H Bonds
    Wei, Wan-Xu
    Czajkowski, Mateusz
    Kuang, Yangjin
    Nguyen, Tu-Anh V.
    Qin, Bo
    Tomanik, Martin
    ACS CATALYSIS, 2024, 14 (09) : 6535 - 6546