Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2011(15): 2490-2494
DOI: 10.1055/s-0030-1260109
DOI: 10.1055/s-0030-1260109
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkRevisited Synthesis of Aryl-H-phosphinates
Further Information
Received
19 April 2011
Publication Date:
14 July 2011 (online)
Publication History
Publication Date:
14 July 2011 (online)

Abstract
A systematic study of the reaction conditions for the preparation of pure aryl-H-phosphinate esters, originally developed by Sander and optimized by Petneházy, 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.
Key words
phosphonites - phosphinates - aryl-H-phosphinates - triethyl phosphite - hydrolysis - Grignard reagent
- 1a
Pirat J.-L,Virieux D,Clarion L,Volle J.-N,Bakalara N,Mersel M,Montbrun J, andCristau H.-J. inventors; PCT WO 2009004096. ; Chem. Abstr. 2009, 150, 98586Reference Ris Wihthout Link - 1b
Volle J.-N.Filippini D.Krawczyk B.Kaloyanov N.Van der Lee A.Maurice T.Pirat J.-L.Virieux D. Org. Biomol. Chem. 2010, 8: 1438Reference Ris Wihthout Link - 2a
van der Knapp ThA.Klebach ThC.Lourens R.Vos M.Bickelhaupt F. J. Am. Chem. Soc. 1983, 105: 4026Reference Ris Wihthout Link - 2b
Yoshifuji M.Hirano M.Toyota K. Tetrahedron Lett. 1993, 34: 1043Reference Ris Wihthout Link - 2c
Wang F.Schwabacher A. Tetrahedron Lett. 1999, 40: 7641Reference Ris Wihthout Link - 3
Yoshifuji M.Nakazawa M.Sato T.Toyota K. Tetrahedron 2000, 56: 43 - 4a
Lei H.Stoakes MS.Schwabacher AW. Synthesis 1992, 1255Reference Ris Wihthout Link - 4b
Lei H.Stoakes MS.Herath KPB.Lee J.Schwabacher AW. J. Org. Chem. 1994, 59: 4206Reference Ris Wihthout Link - 4c
Schwabacher AW.Stefanescu AD. Tetrahedron Lett. 1996, 37: 425Reference Ris Wihthout Link - 4d
Schwabacher AW.Stefanescu AD.Rehman A. J. Org. Chem. 1999, 64: 1784Reference Ris Wihthout Link - 5
Schuman M.Lopez X.Karplus M.Gouverneur V. Tetrahedron 2001, 57: 10299 - 6a
Deprèle S.Montchamp J.-L. J. Organomet. Chem. 2002, 643-644: 154Reference Ris Wihthout Link - 6b
Bravo-Altamirano K.Huang Z.Montchamp J.-L. Tetrahedron 2005, 61: 6315Reference Ris Wihthout Link - 7
Petneházy I.Jászay ZM.Szabó A.Everaert K. Synth. Commun. 2003, 33: 1665 - 8
Sander M. Chem. Ber. 1960, 93: 1220 - 9
Xu H.Ekoue-Kovi K.Wolf C. J. Org. Chem. 2008, 73: 7638 - 10
Kiss NZ.Keglevich G.Ludanyi K.Drahos L. Synth. Commun. 2009, 39: 2392Reference Ris Wihthout Link - 11
Vinogradov LI.Zimin MG.Samitov YY.Pudovik AN. Zh. Obshch. Khim. 1972, 42: 1724 - 12
Dahn H.Van Toan V.Ung-Truong M.-N. Magn. Reson. Chem. 1992, 30: 1089 - 13
Parsy CC,Alexandre F.-R,Surleraux D,Derock M, andLeroy F. inventors; US 2009/0202480. ; Chem. Abstr. 2009, 151, 267307Reference Ris Wihthout Link