PALLADIUM-CATALYZED ALLYLATION OF α-NITROACETATES WITH PROPYNES

被引:1
|
作者
Yao, Shanshan [1 ]
Liu, Jidan [1 ]
Yang, Zhiyong [1 ]
Gui, Qingwen [1 ]
Chen, Xiang [1 ]
Tan, Ze [1 ]
Li, Ping [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
基金
美国国家科学基金会;
关键词
alpha-Nitroacetate; allylation; Pd catalysis; propynes; Tsuji-Trost reaction; NEUTRAL CONDITIONS; ALKYNES; PRONUCLEOPHILES; ALKYLATION; SUBSTITUTION; DERIVATIVES;
D O I
10.1080/00397911.2014.928939
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel way to synthesize allylated alpha-nitroacetates under Pd catalysis has been described. Reactions of propynes with diverse alpha-nitroacetates in the presence of a catalytic amount of Pd(PPh3)(4) and HOAc in 1,4-dioxane afforded the corresponding allylated products in good yields. Compared with other known methods, this method of synthesizing allylated alpha-nitroacetates generated no waste and needed neither a stoichiometric amount of base nor a leaving group.
引用
下载
收藏
页码:3165 / 3172
页数:8
相关论文
共 50 条
  • [31] Stereocontrolled O-Glycosylation with Palladium-Catalyzed Decarboxylative Allylation
    Xiang, Shaohua
    He, Jingxi
    Tan, Yu Jia
    Liu, Xue-Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (23): : 11473 - 11482
  • [32] Palladium-Catalyzed Allylation of Endocyclic 1-Azaallyl Anions
    Yang, Xiaoyu
    Zhang, Biao
    Ruan, Junhao
    Duanmu, Kaining
    Chen, Weijie
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12): : 8896 - 8905
  • [33] Palladium-catalyzed direct allylation of fluorinated benzothiadiazoles with allyl chlorides
    Wang, Jing
    Yu, Yan-Bo
    Zhang, Xingang
    TETRAHEDRON, 2018, 74 (44) : 6329 - 6334
  • [34] Palladium-catalyzed N-allylation of imides with allyl alcohol
    Qu, JP
    Ishimura, Y
    Nagato, N
    NIPPON KAGAKU KAISHI, 1996, (06) : 525 - 529
  • [35] PALLADIUM-CATALYZED CARBONYL ALLYLATION OF ALDEHYDES BY ALLYLIC CYCLIC CARBONATES
    KANG, SK
    PARK, DC
    PARK, CH
    JANG, SB
    SYNTHETIC COMMUNICATIONS, 1995, 25 (09) : 1359 - 1366
  • [36] PALLADIUM-CATALYZED INTRAMOLECULAR CARBONYL ALLYLATION VIA CLAISEN REARRANGEMENT
    MASUYAMA, Y
    NIMURA, Y
    KURUSU, Y
    TETRAHEDRON LETTERS, 1992, 33 (43) : 6477 - 6478
  • [37] Palladium-catalyzed asymmetric umpolung allylation of imines with allylic alcohols
    Qiao, Xiang-Chen
    Zhu, Shou-Fei
    Chen, Wang-Qiao
    Zhou, Qi-Lin
    TETRAHEDRON-ASYMMETRY, 2010, 21 (9-10) : 1216 - 1220
  • [38] Ferrocenylphosphine-amide ligands for palladium-catalyzed asymmetric allylation
    Boaz, NW
    Ponasik, JA
    Large, SE
    Debenham, SD
    TETRAHEDRON-ASYMMETRY, 2004, 15 (14) : 2151 - 2154
  • [39] Palladium-catalyzed β-allylation of 2,3-disubstituted indoles
    Kagawa, Natsuko
    Malerich, Jeremiah P.
    Rawal, Viresh H.
    ORGANIC LETTERS, 2008, 10 (12) : 2381 - 2384
  • [40] Palladium-Catalyzed Allenamide Carbopalladation/Allylation with Active Methine Compounds
    Zhu, Xiaoyi
    Li, Ruibo
    Yao, Hequan
    Lin, Aijun
    ORGANIC LETTERS, 2021, 23 (12) : 4630 - 4634