4.4.22 Product Subclass 22: Silyl Phosphines

Abstract

This chapter is a revision of the earlier Science of Synthesis contribution, published in 2001, describing methods for the synthesis of silyl phosphines and their applications in organic synthesis. In contrast to the earlier contribution, in which the applications of silyl phosphines were described only very briefly, in this revision the applications of silyl phosphines are classified and summarized and include recent improvements, especially with regard to P—C bond formation.

Key words

silyl phosphines - phosphines - phosphorus compounds - phosphaalkenes - phosphaalkynes - phosphorus heterocycles - silyl ethers

• 1 Fritz G, Scheer P. Chem. Rev. 2000; 100: 3341

• 2 Thottathil J, In: Handbook of Organophosphorus Chemistry Engel R. Marcel Decker New York 1992; 82

• 3 Hayashi M. Chem. Rec. 2009; 9: 236

• 4 Healy MD, Laibinis PE, Stupik PD, Barron AR. J. Chem. Soc., Chem. Commun. 1989; 359

• 5 Dubac J, Cavezzan J, Mazerolles P, Escudie J, Couret C, Satge J. J. Organomet. Chem. 1979; 174: 263

• 6 Martens R, du Mont W.-W, Lange L. Z. Naturforsch., B 1991; 46: 1609

• 7 Müller LP, du Mont W.-W, Jeske J, Jones PG. Chem. Ber. 1995; 128: 615

• 8 du Mont W.-W, Müller LP, Müller L, Vollbrecht S, Zanin A. J. Organomet. Chem. 1996; 521: 417

• 9 Müller LP, Zanin A, du Mont W.-W, Jeske J, Martens R, Jones PG. Chem. Ber./Recl. 1997; 130: 377

• 10 Shu R, Hao L, Harrod JF, Woo H.-G, Samuel E. J. Am. Chem. Soc. 1998; 120: 12 988

• 11 Geier SJ, Stephan DW. Chem. Commun. (Cambridge) 2008; 99

• 12 Geier SJ, Stephan DW. Chem. Commun. (Cambridge) 2010; 46: 1026

• 13 Klingebiel U, Vater N, Clegg W, Haase M, Sheldrick GM. Z. Naturforsch., B 1983; 38: 1557

• 14 Wiberg N, Schuster H. Chem. Ber. 1991; 124: 93

• 15 Uhlig W, Tzschach A. Z. Anorg. Allg. Chem. 1989; 576: 281

• 16 Becker G, Hölderich W. Chem. Ber. 1975; 108: 2484

• 17 Askham FR, Stanley GG, Marques EC. J. Am. Chem. Soc. 1985; 107: 7423

• 18 Cossairt BM, Cummins CC. New J. Chem. 2010; 34: 1533

• 19 Niecke E, Westermann H. Synthesis 1988; 330

• 20 Bruker AB, Balashova LD, Soborovskii LZ. Dokl. Akad. Nauk SSSR 1960; 135: 843 Chem. Abstr. 1961; 55: 13 301

• 21 Leffler AJ, Teach EG. J. Am. Chem. Soc. 1960; 82: 2710

• 22 Parshall GW, Lindsey Jr RV. J. Am. Chem. Soc. 1959; 81: 6273

• 23 Schumann H, Rösch L. J. Organomet. Chem. 1973; 55: 257

• 24 Schumann H, Rösch L. Chem. Ber. 1974; 107: 854

• 25 Schumann H, du Mont W.-W. Chem. Ber. 1975; 108: 2261

• 26 Schubert DM, Norman AD. Inorg. Chem. 1985; 24: 1107

• 27 Becker G, Mundt O, Rössler M, Schneider E. Z. Anorg. Allg. Chem. 1978; 443: 42

• 28 Yoshifuji M, Toyota K, Shibayama K, Inamoto N. Chem. Lett. 1983; 1653

• 29 Kuchen W, Buchwald H. Angew. Chem. 1957; 69: 307

• 30 Kuchen W, Buchwald H. Chem. Ber. 1959; 92: 227

• 31 Goldsberry R, Cohn K. Inorg. Synth. 1972; 13: 26

• 32 Kremer PW, Most JT, Cowles JM, Borsub L, Gamiel A, Cremer SE, In: Organometallic Syntheses King RB, Eisch JJ. Elsevier Amsterdam 1988; 4. 511

• 33 Luther III GW, Beyerle G. Inorg. Synth. 1977; 17: 186

• 34 Appel R, Geisler K. J. Organomet. Chem. 1976; 112: 61

• 35 Hayashi M, Matsuura Y, Nishimura Y, Yamasaki T, Imai Y, Watanabe Y. J. Org. Chem. 2007; 72: 7798

• 36 Schäfer H, Fritz G, Hölderich W. Z. Anorg. Allg. Chem. 1977; 428: 222

• 37 Traut S, von Hänisch C, Kathagen H.-J. Eur. J. Inorg. Chem. 2009; 777

• 38 Fritz G, Schäfer H. Z. Anorg. Allg. Chem. 1971; 385: 243

• 39 Norman AD, Wingeleth DC. Inorg. Chem. 1970; 9: 98

• 40 Baudler M, Scholz G, Oehlert W. Z. Naturforsch., B 1989; 44: 627

• 41 Fritz G, Schäfer H. Z. Anorg. Allg. Chem. 1974; 406: 167

• 42 Chan VS, Bergman RG, Toste FD. J. Am. Chem. Soc. 2007; 129: 15 122

• 43 Trepohl VT, Oestreich M. Chem. Commun. (Cambridge) 2007; 3300

• 44 Hayashi M, Matsuura Y, Watanabe Y. Tetrahedron Lett. 2004; 45: 9167

• 45 Tunney SE, Stille JK. J. Org. Chem. 1987; 52: 748

• 46 Wolfsberger W, Bank J, Werner H. Z. Naturforsch., B 1995; 50: 1319

• 47 Trepohl VT, Fröhlich R, Oestreich M. Tetrahedron 2009; 65: 6510

• 48 Martens R, du Mont W.-W. Chem. Ber. 1992; 125: 657

• 49 Schubert DM, Norman AD. Inorg. Chem. 1984; 23: 4130

• 50 Schubert DM, Brandt PF, Norman AD. Inorg. Chem. 1996; 35: 6204

• 51 Brandt PF, Schubert DM, Norman AD. Inorg. Chem. 1997; 36: 1728

• 52 Issleib K, Kühne U, Krech F. Phosphorus Sulfur Relat. Elem. 1985; 21: 367

• 53 Fritz G, Becker G, Kummer D. Z. Anorg. Allg. Chem. 1970; 372: 171

• 54 Fritz G, Becker G. Z. Anorg. Allg. Chem. 1970; 372: 180

• 55 Fritz G, Hölderich W. Z. Anorg. Allg. Chem. 1976; 422: 104

• 56 Fritz G, Hölderich W. Z. Anorg. Allg. Chem. 1977; 431: 76

• 57 Uhlig F, Hummeltenberg R. J. Organomet. Chem. 1993; 452: C9.

• 58 Uhlig F, Gremler S, Dargatz M, Scheer M, Herrmann E. Z. Anorg. Allg. Chem. 1991; 606: 105

• 59 Hölderich W, Seyferth D. J. Organomet. Chem. 1978; 153: 299

• 60 Hayashi M, Matsuura Y, Watanabe Y. Tetrahedron Lett. 2004; 45: 1409

• 61 Brisdon AK, Herbert CJ. Chem. Commun. (Cambridge) 2009; 6658

• 62 Fild M, Jones PG, Ruhnau K. J. Fluorine Chem. 1991; 54: 387

• 63 Clarke ML, Orpen AG, Pringle PG, Turley E. Dalton Trans. 2003; 4393

• 64 Hirano K, Yorimitsu H, Oshima K. Org. Lett. 2004; 6: 4873

• 65 Kazankova MA, Chirkov EA, Kochetkov AN, Efimova IV, Beletskaya IP. Tetrahedron Lett. 1999; 40: 573

• 66 Goryunov LI, Grobe J, Shteingarts VD, Krebs B, Lindemann A, Würthwein E.-U, Mück-Lichtenfeld C. Chem.–Eur. J. 2000; 6: 4612

• 67 Hayashi M, Yamasaki T, Kobayashi Y, Imai Y, Watanabe Y. Eur. J. Org. Chem. 2009; 4956

• 68 Lindner E, Frey G. Chem. Ber. 1980; 113: 3268

• 69 Lindner E, Hübner D. Chem. Ber. 1983; 116: 2574

• 70 Lindner E, Tamoutsidis E. Chem. Ber. 1983; 116: 3141

• 71 Becker G, Mundt O. Z. Anorg. Allg. Chem. 1980; 462: 130

• 72 Matsuura Y, Yamasaki T, Watanabe Y, Hayashi M. Tetrahedron: Asymmetry 2007; 18: 2129

• 73 Kolodiazhnyi OI, Guliaiko IV, Kolodiazhna AO. Tetrahedron Lett. 2004; 45: 6955

• 74 Kolodyazhnaya AO, Kukhar’ VP, Kolodyazhnyi OI. Zh. Obshch. Khim. 2004; 74: 1045 Russ. J. Gen. Chem. (Engl. Transl.) 2004; 74: 965

• 75 Hayashi M, Matsuura Y, Watanabe Y. Tetrahedron Lett. 2005; 46: 5135

• 76 Trepohl VT, Mori S, Itami K, Oestreich M. Org. Lett. 2009; 11: 1091

• 77 Hayashi M, Matsuura Y, Watanabe Y. J. Org. Chem. 2006; 71: 9248

• 78 Reisser M, Maier A, Maas G. Synlett 2002; 1459

• 79 Reisser M, Maier A, Maas G. Eur. J. Org. Chem. 2003; 2071

• 80 Hayashi M, Matsuura Y, Kurihara K, Maeda D, Nishimura Y, Morita E, Okasaka M, Watanabe Y. Chem. Lett. 2007; 36: 634

• 81 Armitage DA, In: Comprehensive Organometallic Chemistry Wilkinson G, Stone FGA, Abel EW. Pergamon Oxford 1984; 2. 146

• 82 Becker G. Z. Anorg. Allg. Chem. 1976; 423: 242

• 83 Yoshifuji M, Toyota K, Inamoto N. Tetrahedron Lett. 1985; 26: 1727

• 84 Yoshifuji M, Toyota K, Matsuda I, Niitsu T, Inamoto N, Hirotsu K, Higuchi T. Tetrahedron 1988; 44: 1363

• 85 Yoshifuji M, Yoshimura H, Toyota K. Chem. Lett. 1990; 827

• 86 Yoshifuji M, Toyota K, Shibayama K, Inamoto N. Tetrahedron Lett. 1984; 25: 1809

• 87 Yoshifuji M, Toyota K, Inamoto N. J. Chem. Soc., Chem. Commun. 1984; 689

• 88 Karsch HH, Reisacher H.-U, Müller G. Angew. Chem. 1984; 96: 619 Angew. Chem. Int. Ed. Engl. 1984; 23: 618

• 89 Bates JI, Patrick BO, Gates DP. New J. Chem. 2010; 34: 1660

• 90 Wright VA, Patrick BO, Schneider C, Gates DP. J. Am. Chem. Soc. 2006; 128: 8836

• 91 Becker G. Z. Anorg. Allg. Chem. 1977; 430: 66

• 92 Märkl G, Sejpka H. Tetrahedron Lett. 1986; 27: 171

• 93 Becker G, Gresser G, Uhl W. Z. Naturforsch., B 1981; 36: 16

• 94 Rösch W, Hees U, Regitz M. Chem. Ber. 1987; 120: 1645

• 95 Schmidpeter A, Willhalm A. Angew. Chem. 1984; 96: 901 Angew. Chem. Int. Ed. Engl. 1984; 23: 903

• 96 Märkl G, Dorfmeister G. Tetrahedron Lett. 1986; 27: 4419

• 97 Märkl G, Dorfmeister G. Tetrahedron Lett. 1987; 28: 1089

• 98 Märkl G, Pflaum S. Tetrahedron Lett. 1987; 28: 1511

• 99 Märkl G, Dörges C. Angew. Chem. 1991; 103: 82 Angew. Chem. Int. Ed. Engl. 1991; 30: 106

• 100 Märkl G, Lieb F, Merz A. Angew. Chem. 1967; 79: 475 Angew. Chem. Int. Ed. Engl. 1967; 6: 458

• 101 Märkl G, Pflaum S. Tetrahedron Lett. 1986; 27: 4415

• 102 Märkl G, Dorfmeister G. Tetrahedron Lett. 1987; 28: 1093