The Synthesis and Reactivity of Phosphinous Acid-Boranes

Marek Stankevič; K. Michał Pietrusiewicz

doi:10.1055/s-2005-861878

PAPER

The Synthesis and Reactivity of Phosphinous Acid-Boranes

Marek Stankevič^a, K. Michał Pietrusiewicz*^a,b
^a Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland
^b Department of Organic Chemistry, Maria Curie-Skodowska University, ul. Gliniana 33, 20-614 Lublin, Poland
Fax: +48(22)6326681; e-Mail: kmp@icho.edu.pl;

Abstract

Alle Artikel dieser Rubrik

Abstract

Phosphinic acid chlorides are converted directly into phosphinous acid-boranes in a process utilizing BH₃·THF complex as a reducing agent. The process is general and affords phosphinous acid-boranes in good to very high yields. Phosphinous acid-boranes have been found to react readily with alkylating, acylating, reducing, halogenating and deborating agents to produce the corresponding phosphinous acid-borane esters, phosphinous acid-borane anhydrides, sec-phosphine oxides, sec-phosphine boranes and phosphinic acid halides, respectively. The efficient procedures for these conversions have been developed and their scope has been outlined.

Key words

phosphorus - boron - alkylation - acylation - halogenation

Volltext

Referenzen

References

1a Brunel JM. Faure B. Maffei M. Coord. Chem. Rev. 1998, 178-180: 665

1b Ohf H. Holz J. Quirmbach M. Börner A. Synthesis 1998, 1391

2a Imamoto T. Oshiki T. Onozawa T. Kusumoto T. Sato K. J. Am. Chem. Soc. 1990, 112: 5244

2b Imamoto T. Oshiki T. Onozawa T. Matsuo M. Hikosaka T. Yanagawa M. Heteroat. Chem. 1992, 3: 563

2c Imamoto T. Tsuruta H. Chem. Lett. 1996, 707

2d Muci AR. Campos KR. Evans DA. J. Am. Chem. Soc. 1995, 117: 9075

3a Lam H. Aldous DJ. Hii KK. Tetrahedron Lett. 2003, 44: 5213

3b Longeau A. Durand S. Spiegel A. Knochel P. Tetrahedron: Asymmetry 1997, 8: 987

3c Jugé S. Stephan M. Laffitte JA. Genêt JP. Tetrahedron Lett. 1990, 31: 6357

3d Jugé S. Stephan M. Merdès R. Genêt JP. Halut-Despartes S. J. Chem. Soc., Chem. Commun. 1993, 531

3e Jugé S. Stephan M. Achi S. Genêt JP. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 49/50: 267

3f Ramsden JA. Brown JM. Tetrahedron: Asymmetry 1994, 5: 2033

3g Bauduin C. Moulin D. Kaloun EB. Darcel C. Jugé S. J. Org. Chem. 2003, 68: 4293

3h Nagata K. Matsukawa S. Imamoto T. J. Org. Chem. 2000, 65: 4185

4a Hoge G. J. Am. Chem. Soc. 2003, 125: 10219

4b Oshiki T. Imamoto T. J. Am. Chem. Soc. 1992, 114: 3975

4c Nettekoven U. Widhalm M. Kamer PCJ. van Leeuwen PWNM. Tetrahedron: Asymmetry 1997, 8: 3185

4d Oshiki T. Imamoto T. Bull. Chem. Soc. Jpn. 1990, 63: 3719

4e Oshiki T. Hikosaka T. Imamoto T. Tetrahedron Lett. 1991, 32: 3371

4f Imamoto T. Tsuruta H. Wada Y. Masuda H. Yamaguchi K. Tetrahedron Lett. 1995, 36: 8271

5 Schmidbaur H. J. Organomet. Chem. 1980, 200: 287

6a Köster R. Tsay Y.-H. Synoradzki L. Chem. Ber. 1987, 120: 1117

6b Uziel J. Stéphan M. Kaloun EB. Genêt JP. Jugé S. Bull. Soc. Chim. Fr. 1997, 134: 379

7 Stankevič M. Pietrusiewicz KM. Synlett 2003, 1012

8 Stankevič M. Andrijewski G. Pietrusiewicz KM. Synlett 2004, 313

9 See, for example: Pietrusiewicz KM. Wiśniewski W. Zabocka M. Tetrahedron 1989, 45: 337

10 McKinstry L. Livinghouse T. Tetrahedron Lett. 1994, 35: 9319

11a Maier L. Dietl PJ. Phosphorus, Sulfur, Silicon Relat. Elem. 1996, 115: 723

11b Korpiun O. Lewis RA. Chickos J. Mislow K. J. Am. Chem. Soc. 1968, 90: 4842