Revisited Synthesis of Aryl-H-phosphinates

被引:12
作者
Volle, Jean-Noel [1 ]
Filippini, Damien [1 ]
Midrier, Camille [1 ]
Sobecki, Michal [2 ]
Drag, Marcin [2 ]
Virieux, David [1 ]
Pirat, Jean-Luc [1 ]
机构
[1] ENSCM, Inst Charles Gerhardt, UMR5253, AM2N, F-34296 Montpellier 5, France
[2] Wroclaw Univ Technol, Fac Chem, Dept Med Chem & Microbiol, PL-50370 Wroclaw, Poland
来源
SYNTHESIS-STUTTGART | 2011年 / 15期
关键词
phosphonites; phosphinates; aryl-H-phosphinates; triethyl phosphite; hydrolysis; Grignard reagent; ACID; ESTERS; HALIDES; BOND;
D O I
10.1055/s-0030-1260109
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A systematic study of the reaction conditions for the preparation of pure aryl-H-phosphinate esters, originally developed by Sander and optimized by Petnehazy, is reported. The influence of the reaction concentration has been investigated for the formation of phosphonite intermediates via direct addition of triethyl phosphite to the appropriate Grignard reagent. Subsequent hydrolysis of the phosphonites under acidic conditions gives various aryl-H-phosphinates in high yields and purities.
引用
收藏
页码:2490 / 2494
页数:5
相关论文
共 20 条
  • [1] Palladium-catalyzed phosphorus-carbon bond formation: cross-coupling reactions of alkyl phosphinates with aryl, heteroaryl, alkenyl, benzylic, and allylic halides and triflates
    Bravo-Altamirano, K
    Huang, ZH
    Montchamp, JL
    [J]. TETRAHEDRON, 2005, 61 (26) : 6315 - 6329
  • [2] NMR OF TERMINAL OXYGEN .9. O-17 NMR OF THE P-O DOUBLE-BOND - PHOSPHINE OXIDES, PHOSPHINATES, PHOSPHONATES, ACYLPHOSPHONATES AND RELATED-COMPOUNDS
    DAHN, H
    TOAN, VV
    UNGTRUONG, MN
    [J]. MAGNETIC RESONANCE IN CHEMISTRY, 1992, 30 (11) : 1089 - 1096
  • [3] A novel and convenient preparation of hypophosphite esters
    Deprèle, S
    Montchamp, JL
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 643 : 154 - 163
  • [4] Novel Synthesis of Phosphinates by the Microwave-Assisted Esterification of Phosphinic Acids
    Kiss, Nora Zsuzsa
    Ludanyi, Krisztina
    Drahos, Laszlo
    Keglevich, Gyorgy
    [J]. SYNTHETIC COMMUNICATIONS, 2009, 39 (13) : 2392 - 2404
  • [5] LEI HY, 1992, SYNTHESIS-STUTTGART, P1255
  • [6] EFFICIENT SYNTHESIS OF A PHOSPHINATE BIS-AMINO ACID AND ITS USE IN THE CONSTRUCTION OF AMPHIPHILIC PEPTIDES
    LEI, HY
    STOAKES, MS
    HERATH, KPB
    LEE, JH
    SCHWABACHER, AW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) : 4206 - 4210
  • [7] PARSY CC, 2009, Patent No. 20090202480
  • [8] Convenient one pot synthesis of phosphonites and H-phosphinates
    Petneházy, I
    Jászay, ZM
    Szabó, A
    Everaert, K
    [J]. SYNTHETIC COMMUNICATIONS, 2003, 33 (10) : 1665 - 1674
  • [9] Pirat J.-L., 2009, PCT Int. Appl, Patent No. [2009004096, 2009004096 A1]
  • [10] HERSTELLUNG UND REAKTIONEN VON PHOSPHONIGSAUREESTERN UND PHOSPHINIGSAUREESTERN
    SANDER, M
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1960, 93 (05): : 1220 - 1230