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
  • [1] Bu4NI-Catalyzed Dehydrogenative Coupling of Diary! Phosphinic Acids with C(sp3)-H Bonds of Arenes
    Xiong, Biquan
    Wang, Gang
    Zhou, Congshan
    Liu, Yu
    Zhang, Panliang
    Tang, Kewen
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (02): : 993 - 999
  • [2] Pd(II)-catalyzed decarboxylative acylation of phenylacetamides with α-oxocarboxylic acids via C-H bond activation
    Park, Jihye
    Kim, Minyoung
    Sharma, Satyasheel
    Park, Eonjeong
    Kim, Aejin
    Lee, Sang Hwi
    Kwak, Jong Hwan
    Jung, Young Hoon
    Kim, In Su
    CHEMICAL COMMUNICATIONS, 2013, 49 (16) : 1654 - 1656
  • [3] Copper-catalyzed acyloxylation of the C(sp3)-H bond adjacent to an oxygen by a cross-dehydrogenative coupling approach
    Raju, Kammari Bal
    Kumar, Bejjanki Naveen
    Nagaiah, Kommu
    RSC ADVANCES, 2014, 4 (92) : 50795 - 50800
  • [4] Palladium-catalyzed decarboxylative C3-acylation of benzofurans and benzothiophenes with α-oxocarboxylic acids via direct sp2 C-H bond activation
    Gong, Wei-Jie
    Liu, De-Xian
    Li, Fei-Long
    Gao, Jun
    Li, Hong-Xi
    Lang, Jian-Ping
    TETRAHEDRON, 2015, 71 (08) : 1269 - 1275
  • [5] Palladium-Catalyzed β-Acyloxylation of Simple Amide via sp3 C-H Activation
    Zhou, Lihong
    Lu, Wenjun
    ORGANIC LETTERS, 2014, 16 (02) : 508 - 511
  • [6] KI-catalyzed imidation of sp3 C-H bond adjacent to amide nitrogen atom
    Lao, Zhi-Qi
    Zhong, Wen-He
    Lou, Qing-Hua
    Li, Zhong-Jun
    Meng, Xiang-Bao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (39) : 7869 - 7871
  • [7] Metal-catalyzed functionalization of sp3 C-H bond
    Yun, Sang Young
    Wang, Kung-Pern
    Mamidipalli, Phani
    Lee, Nam-Kyu
    Lee, Daesung
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [8] Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles
    Campos, Kevin R.
    CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1069 - 1084
  • [9] Nickel-Catalyzed sp3 C-H Bond Activation from Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Amides
    Zhang, Jia-Xiang
    Wang, Yan-Jing
    Wang, Nai-Xing
    Zhang, Wei
    Bai, Cui-Bing
    Li, Yi-He
    Wen, Jia-Long
    SYNLETT, 2014, 25 (11) : 1621 - 1625
  • [10] Decarboxylative Acylation of Arenes with α-Oxocarboxylic Acids via Palladium-Catalyzed C-H Activation
    Li, Mingzong
    Ge, Haibo
    ORGANIC LETTERS, 2010, 12 (15) : 3464 - 3467