Palladium-Catalyzed Allylation/Benzylation of H-Phosphinate Esters with Alcohols

被引:10
|
作者
Fers-Lidou, Anthony [1 ]
Berger, Olivier [1 ]
Montchamp, Jean-Luc [1 ]
机构
[1] Texas Christian Univ, Dept Chem & Biochem, TCU Box 298860, Ft Worth, TX 76129 USA
基金
美国国家科学基金会;
关键词
palladium; cross-coupling; alcohols; H-phosphinate esters; allylation; benzylation; P-STEREOGENIC COMPOUNDS; ALLYLIC ALCOHOLS; HYPOPHOSPHOROUS ACID; ESTERIFICATION; ALLYLATION;
D O I
10.3390/molecules21101295
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The Pd-catalyzed direct alkylation of H-phosphinic acids and hypophosphorous acid with allylic/benzylic alcohols has been described previously. Here, the extension of this methodology to H-phosphinate esters is presented. The new reaction appears general, although its scope is narrower than with the acids, and its mechanism is likely different. Various alcohols are examined in their reaction with phosphinylidene compounds (RRP)-R-1-P-2(O)H.
引用
收藏
页数:15
相关论文
共 50 条
  • [41] Palladium catalyzed direct benzylation/allylation of malonates with alcohols - in situ C-O bond activation
    Cao, Xueqin
    Zhang, Yugen
    GREEN CHEMISTRY, 2016, 18 (09) : 2638 - 2641
  • [42] Palladium-Catalyzed Decarboxylative Benzylation of Diphenylglycinate Imines
    Fields, Wendy H.
    Chruma, Jason J.
    ORGANIC LETTERS, 2010, 12 (02) : 316 - 319
  • [43] Palladium-catalyzed asymmetric decarboxylative benzylation of alkynes
    Mendis, Shehani N.
    Tunge, Jon A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [44] Domino Catalysis: Palladium-Catalyzed Carbonylation of Allylic Alcohols to ,-Unsaturated Esters
    Liu, Qiang
    Wu, Lipeng
    Jiao, Haijun
    Fang, Xianjie
    Jackstell, Ralf
    Beller, Matthias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (31) : 8064 - 8068
  • [45] Efficient and selective palladium-catalyzed direct aerobic oxidation of alcohols to esters
    Hu, Yongke
    Li, Bindong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [46] Microwave-assisted palladium-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation
    Iwasaki, Masayuki
    Hayashi, Sayuri
    Hirano, Koji
    Yorimitsu, Hideki
    Oshima, Koichiro
    TETRAHEDRON, 2007, 63 (24) : 5200 - 5203
  • [47] Palladium-Catalyzed ortho C-H Allylation of Tertiary Anilines
    Yuan, Chunchen
    Zhang, Wenlong
    ORGANIC LETTERS, 2025,
  • [48] Palladium-catalyzed allylation of acidic and less nucleophilic anilines using allylic alcohols directly
    Hsu, YC
    Gan, KH
    Yang, SC
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (10) : 1266 - 1269
  • [49] Triethylborane as an efficient promoter for palladium-catalyzed allylation of active methylene compounds with allyl alcohols
    Kimura, M
    Mukai, R
    Tanigawa, N
    Tanaka, S
    Tamaru, Y
    TETRAHEDRON, 2003, 59 (39) : 7767 - 7777
  • [50] PALLADIUM-CATALYZED CARBONYL ALLYLATION OF DIKETO COMPOUNDS BY ALLYLIC ALCOHOLS WITH SNCL2
    MASUYAMA, Y
    TSUNODA, T
    KURUSU, Y
    CHEMISTRY LETTERS, 1989, (09) : 1647 - 1650