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Synlett 2009(2): 287-291
DOI: 10.1055/s-0028-1087671
DOI: 10.1055/s-0028-1087671
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Reduction of Phosphinites, Phosphinates, and Related Species with DIBAL-H
Further Information
Received
1 September 2008
Publication Date:
15 January 2009 (online)
Publication History
Publication Date:
15 January 2009 (online)
Abstract
Diisobutylaluminium hydride has been found to be an excellent reducing agent for phosphinites, phosphinates, and chlorophosphines. By performing reductions in situ, direct synthesis of secondary phosphine boranes from Grignard reagents has been achieved without isolation or purification of any intermediates.
Key words
phosphorus - phosphines - phosphine boranes - reductions
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1a
Busacca CA.Lorenz JC.Grinberg N.Haddad N.Hrapchak M.Latli B.Lee H.Sabila P.Saha A.Sarvestani M.Shen S.Varsolona R.Wei X.Senanayake CH. Org. Lett. 2007, 7: 4277 -
1b
Busacca CA. inventors; US 7 256 314. - 2
Busacca CA.Raju R.Grinberg N.Haddad N.James-Jones P.Lee H.Lorenz JC.Saha A.Senanayake CH. J. Org. Chem. 2008, 73: 1524 - 3
Busacca CA.Lorenz JC.Sabila P.Haddad N.Senanayake CH. Org. Synth. 2007, 84: 242 - For recent examples, see:
-
4a
Ito H.Watanabe A.Sawamaura M. Org. Lett. 2005, 7: 1869 -
4b
Matsumura K.Shimizu H.Saito T.Kumobayashi H. Adv. Synth. Catal. 2003, 345: 180 -
4c
Wolfe B.Livinghouse T. J. Am. Chem. Soc. 1998, 120: 5116 -
5a
Stankevic M.Pietrusiewicz KM. J. Org. Chem. 2007, 72: 816 -
5b
Stankevic M.Andrijewski G.Pietrusiewicz KM. Synlett 2004, 311 -
5c
Brunel JM.Faure B.Maffei M. Coord. Chem. Rev. 1998, 180: 665 -
5d
Imamoto T.Matsuo M.Nonomura T.Kishikawa K.Yanagawa M. Heteroat. Chem. 1993, 4: 475 - For the reduction of chlorophosphine-borane complexes with a variety of reducing agents, see:
-
6a
Lam H.Aldous DJ.Hii KK. Tetrahedron Lett. 2003, 44: 5213 -
7a
Dodds DL.Haddow MF.Orpen AG.Pringle PG.Woodward G. Organometallics 2006, 25: 5937 -
7b
Kuchen W.Buchwald H. Chem. Ber. 1959, 227 - For reviews, see:
-
8a
Engel R.Cohen JLI. Synthesis of Carbon-Phosphorus Bonds CRC Press; Boca Raton: 1988. Chap. 3 and 6. -
8b
Bhattacharya AK.Thyagarajan G. Chem. Rev. 1981, 81: 415 -
9a
Han L.-B.Zhao Z.-Q. J. Org. Chem. 2005, 70: 10121 -
9b
Benschop HP.Platenburg DHJM. J. Chem. Soc., Chem. Commun. 1970, 17: 1098 - Copper:
-
10a
Rao H.Jin Y.Fu H.Jiang Y.Zhao Y. Chem. Eur. J. 2006, 12: 3636 - Palladium:
-
10b
Beletskaya IP.Neganova EG.Veits YA. Russ. J. Org. Chem. 2004, 40: 1782 -
10c
Schuman M.Lopez X.Karplus M.Gouverneur V. Tetrahedron 2001, 57: 10299 - Nickel:
-
10d
Horner L.Lindel H. Chem. Ber. 1985, 118: 676 - 11
Abrunhosa-Thomas I.Sellers CE.Montchamp J.-L. J. Org. Chem. 2007, 72: 2851
References
Wilmad Glass Catalog No. 535-TR-7; www.wilmad-labglass.com.