4.4.5 Product Subclass 5: Disilanes and Oligosilanes

Abstract

This chapter is a revision of the earlier Science of Synthesis contribution describing methods for the preparation and synthetic use of disilanes. This update is extended by coverage of synthetically useful oligosilanes.

Key words

silicon compounds - disilanes - oligosilanes - silylation - protecting groups - radicals - Si—Si bonds - Si—C bonds

• 1 Beckmann J, In: Comprehensive Organometallic Chemistry III Crabtree RH, Mingos DMP. Elsevier Oxford 2007; 3. 409

• 2 Lukevics E, Pudova O. Main Group Met. Chem. 1998; 21: 123

• 3 West R, In: Comprehensive Organometallic Chemistry II Abel EW, Stone FGA, Wilkinson G. Elsevier Oxford 1995; 2. 77

• 4 West R, In: Comprehensive Organometallic Chemistry Wilkinson G, Stone FGA, Abel EW. Pergamon Oxford 1982; 2. 365

• 5 Hengge E. Top. Curr. Chem. 1974; 51: 1

• 6 Hengge E, Janoschek R. Chem. Rev. 1995; 95: 1495

• 7 Hengge E, Stüger H, In: The Chemistry of Organic Silicon Compounds Rappoport Z, Apeloig Y. Wiley Chichester, UK 1998; 2. 2177

• 8 Synthetic Methods of Organometallic and Inorganic Chemistry. Herrmann WA. Thieme; Stuttgart 1996. 2.

• 9 Reagents for Silicon-Mediated Organic Synthesis. Fuchs PL. Wiley; Chichester, UK 2011

• 10 Hollemann AF, Wiberg E. Lehrbuch der Anorganischen Chemie. de Gruyter; Berlin 1995

• 11 Hengge E, Weinberger M. J. Organomet. Chem. 1992; 433: 21

• 12 Laine RM, Sellinger A, In: The Chemistry of Organic Silicon Compounds Rappoport Z, Apeloig Y. Wiley Chichester, UK 1998; 2. 2245

• 13 Miller RD, Michl J. Chem. Rev. 1989; 89: 1359

• 14 D’Amico KL, Manos C, Christensen RL. J. Am. Chem. Soc. 1980; 102: 1777

• 15 Sakurai H. J. Organomet. Chem. 1980; 200: 261

• 16 Sakurai H, Eriyama Y, Kamiyama Y, Nakadaira Y. J. Organomet. Chem. 1984; 264: 229

• 17 Tamao K, Hayashi T, Kumada M. J. Organomet. Chem. 1976; 114: C19

• 18 Sakurai H, Kamiyama Y, Nakadaira Y. J. Am. Chem. Soc. 1975; 97: 931

• 19 Matsumoto H, Matsubara I, Kato T, Shono K, Watanabe H, Nagai Y. J. Organomet. Chem. 1980; 199: 43

• 20 Watanabe H, Kobayashi M, Higuchi K, Nagai Y. J. Organomet. Chem. 1980; 186: 51

• 21 Watanabe H, Kobayashi M, Saito M, Nagai Y. J. Organomet. Chem. 1981; 216: 149

• 22 Pan Y, Mague JT, Fink MJ. Organometallics 1992; 11: 3495

• 23 Murakami M, Yoshida T, Ito Y. Organometallics 1994; 13: 2900

• 24 Sadow AD, Tilley TD. Organometallics 2003; 22: 3577

• 25 Gualco P, Amgoune A, Miqueu K, Ladeira S, Bourissou D. J. Am. Chem. Soc. 2011; 133: 4257

• 26 Takagi N, Sakaki S. J. Am. Chem. Soc. 2012; 134: 11 749

• 27 Traven VF, West R. J. Am. Chem. Soc. 1973; 95: 6824

• 28 Sakurai H, Kira M, Uchida T. J. Am. Chem. Soc. 1973; 95: 6826

• 29 Kumagai J, Yoshida H, Koizumi H, Ichikawa T. J. Phys. Chem. 1994; 98: 13 117

• 30 Marsmann H, Uhlig F, Mikhova B In: Landolt–Börnstein Springer Berlin 2008; 35F

• 31 Morris GA, Freeman R. J. Am. Chem. Soc. 1979; 101: 760

• 32 Helmer BJ, West R. Organometallics 1982; 1: 877

• 33 Koe JR, In: Comprehensive Organometallic Chemistry III Crabtree RH, Mingos DMP. Elsevier Oxford 2007; 3. 549

• 34 Gerval P, Frainnet E, Lain G, Moulines F. Bull. Soc. Chim. Fr. 1974; -154

• 35 Steudel W, Gilman H. J. Am. Chem. Soc. 1960; 82: 6129

• 36 Weidenbruch M, Pellmann A, Pan Y, Pohl S, Saak W, Marsmann H. J. Organomet. Chem. 1993; 450: 67

• 37 Fürstner A, Weidmann H. J. Organomet. Chem. 1988; 354: 15

• 38 Li Z, Iida K, Tomisaka Y, Yoshimura A, Hirao T, Nomoto A, Ogawa A. Organometallics 2007; 26: 1212

• 39 Ohshita J, Hino K, Iwawaki T, Kunai A. J. Electroanal. Chem. 2009; 625: 138

• 40 Loidl B, Fallmann H, Stüger H, Grogger C. Proc.–Electrochem. Soc. 2003; 2003–12: 89

• 41 Grogger C, Loidl B, Stueger H, Kammel T, Pachaly B. J. Organomet. Chem. 2006; 691: 105

• 42 Heinicke J, Mantey S. Heteroat. Chem. 1998; 9: 311

• 43 Lickiss PD, Smith CM. Coord. Chem. Rev. 1995; 145: 75

• 44 Tamao K, Kawachi A. Adv. Organomet. Chem. 1995; 38: 1

• 45 Belzner J, Dehnert U, In: The Chemistry of Organic Silicon Compounds Rappoport Z, Apeloig Y. Wiley Chichester, UK 1998; 2. 779

• 46 Lerner H.-W. Coord. Chem. Rev. 2005; 249: 781

• 47 Uhlig W. Chem. Ber. 1996; 129: 733

• 48 Aitken C, Barry JP, Gauvin F, Harrod JF, Malek A, Rousseau D. Organometallics 1989; 8: 1732

• 49 Rosenberg L, Davis CW, Yao J. J. Am. Chem. Soc. 2001; 123: 5120

• 50 Brown SH, Crabtree RH. J. Am. Chem. Soc. 1989; 111: 2935

• 51 Becerra R, Walsh R. Dalton Trans. 2010; 39: 9217

• 52 West R, Indriksons A. J. Am. Chem. Soc. 1972; 94: 6110

• 53 Gilman H, Smith CL. J. Organomet. Chem. 1967; 8: 245

• 54 Gutekunst G, Brook AG. J. Organomet. Chem. 1982; 225: 1

• 55 Marschner C. Organometallics 2006; 25: 2110

• 56 Still WC. J. Org. Chem. 1976; 41: 3063

• 57 Hatanaka Y, Hiyama T. Tetrahedron Lett. 1987; 28: 4715

• 58 Babin P, Bennetau B, Theurig M, Dunoguès J. J. Organomet. Chem. 1993; 446: 135

• 59 Suginome M, Ito Y. Chem. Rev. 2000; 100: 3221

• 60 Matsuda T, Suda Y, Fujisaki Y. Synlett 2011; 813

• 61 Tobisu M, Ano Y, Chatani N. Chem.–Asian J. 2008; 3: 1585

• 62 Hayashi T, Kawamoto AM, Kobayashi T, Tanaka M. J. Chem. Soc., Chem. Commun. 1990; 563

• 63 Matsuda T, Ichioka Y. Org. Biomol. Chem. 2012; 10: 3175

• 64 Williams NA, Uchimaru Y, Tanaka M. Dalton Trans. 2003; 236

• 65 Roscher A, Bockholt A, Braun T. Dalton Trans. 2009; 1378

• 66 Yamashita H, Kobayashi T, Hayashi T, Tanaka M. Chem. Lett. 1990; 19: 1447

• 67 Haberhauer G, Gleiter R, Irngartinger H, Oeser T, Rominger F. J. Chem. Soc., Perkin Trans. 2 1999; 2093

• 68 Gleiter R, Stahr H, Stadtmüller F, Irngartinger H, Pritzkow H. Tetrahedron Lett. 1995; 36: 4603

• 69 Delpech F, Mansas J, Leuser H, Sabo-Etienne S, Chaudret B. Organometallics 2000; 19: 5750

• 70 Lesbani A, Kondo H, Sato J.-i, Yamanoi Y, Nishihara H. Chem. Commun. (Cambridge) 2010; 46: 7784

• 71 Kato N, Tamura Y, Kashiwabara T, Sanji T, Tanaka M. Organometallics 2010; 29: 5274

• 72 Skjel MK, Houghton AY, Kirby AE, Harrison DJ, McDonald R, Rosenberg L. Org. Lett. 2010; 12: 376

• 73 Gilman H, Shiina K, Aoki D, Gaj BJ, Wittenberg D, Brennan T. J. Organomet. Chem. 1968; 13: 323

• 74 Seitz DE, Ferreira L. Synth. Commun. 1979; 9: 451

• 75 Fritz G, Grunert B. Z. Anorg. Allg. Chem. 1981; 473: 59

• 76 Fleming I, Roberts RS, Smith SC. J. Chem. Soc., Perkin Trans. 1 1998; 1209

• 77 Brown-Wensley KA. Organometallics 1987; 6: 1590

• 78 Corey JY. Chem. Rev. 2011; 111: 863

• 79 Benkeser RA, Landesman H, Foster DJ. J. Am. Chem. Soc. 1952; 74: 648

• 80 Nielsen L, Lindsay KB, Faber J, Nielsen NC, Skrydstrup T. J. Org. Chem. 2007; 72: 10 035

• 81 George MV, Peterson DJ, Gilman H. J. Am. Chem. Soc. 1960; 82: 403

• 82 Barbaro A, Cuadrado P, González AM, Pulido FJ, Fleming I. J. Chem. Soc., Perkin Trans. 1 1991; 2811

• 83 Ishikawa M, Kumada M, Sakurai H. J. Organomet. Chem. 1970; 23: 63

• 84 Stüger H. J. Organomet. Chem. 1992; 433: 11

• 85 Cunico RF. Synth. React. Inorg. Met.-Org. Chem. 1986; 16: 33

• 86 Matyjaszewski K, Chen YL. J. Organomet. Chem. 1988; 340: 7

• 87 Herzog U, Roewer G. J. Organomet. Chem. 1997; 544: 217

• 88 Hengge E, Weinberger M. J. Organomet. Chem. 1992; 441: 397

• 89 Weinberger M Ph.D. Dissertation, TU Graz 1992

• 90 Kornev AN. Russ. Chem. Rev. (Engl. Transl.) 2004; 73: 1065

• 91 Boxer MB, Albert BJ, Yamamoto H. Aldrichimica Acta 2009; 42: 3

• 92 Wiberg N Xth International Symposium on Organosilicon Chemistry, Poznan, Poland 1993

• 93 Henkel S, Klinkhammer KW, Schwarz W. Angew. Chem. 1994; 106: 721 Angew. Chem. Int. Ed. Engl. 1994; 33: 681

• 94 Bock H, Meuret J, Ruppert K. Angew. Chem. 1993; 105: 413 Angew. Chem. Int. Ed. Engl. 1993; 32: 414

• 95 Roos C, McGibbon GA, Brook MA. Can. J. Chem. 1996; 74: 1470

• 96 Brook MA, Gottardo C, Balduzzi S, Mohamed M. Tetrahedron Lett. 1997; 38: 6997

• 97 Kopping B, Chatgilialoglu C, Zehnder M, Giese B. J. Org. Chem. 1992; 57: 3994

• 98 Alberti A, Chatgilialoglu C. Tetrahedron 1990; 46: 3963

• 99 Chatgilialoglu C, Timokhin VI. Adv. Organomet. Chem. 2008; 57: 117

• 100 Chatgilialoglu C. Chem.–Eur. J. 2008; 14: 2310

• 101 Brazeau J.-F. Synlett 2007; 1972

• 102 Rouquet G, Robert F, Méreau R, Castet F, Landais Y. Chem.–Eur. J. 2011; 17: 13 904

• 103 Brook MA, Balduzzi S, Mohamed M, Gottardo C. Tetrahedron 1999; 55: 10 027

• 104 Balduzzi S, Brook MA. Tetrahedron 2000; 56: 1617

• 105 Boxer MB, Yamamoto H. J. Am. Chem. Soc. 2006; 128: 48

• 106 Brady PB, Yamamoto H. Angew. Chem. 2012; 124: 1978 Angew. Chem. Int. Ed. 2012; 51: 1942

• 107 Boxer MB, Yamamoto H. Org. Lett. 2008; 10: 453

• 108 Boxer MB, Akakura M, Yamamoto H. J. Am. Chem. Soc. 2008; 130: 1580

• 109 Albert BJ, Yamaoka Y, Yamamoto H. Angew. Chem. 2011; 123: 2658 Angew. Chem. Int. Ed. 2011; 50: 2610

• 110 Boxer MB, Yamamoto H. Org. Lett. 2005; 7: 3127

• 111 Brook AG, Abdesaken F, Gutekunst B, Gutekunst G, Kallury RK. J. Chem. Soc., Chem. Commun. 1981; 191

• 112 Ottosson H, Steel PG. Chem.–Eur. J. 2006; 12: 1576

• 113 Sanganee MJ, Steel PG, Whelligan DK. J. Org. Chem. 2003; 68: 3337

• 114 Berry MB, Griffiths RJ, Sanganee MJ, Steel PG, Whelligan DK. Org. Biomol. Chem. 2004; 2: 2381

• 115 Berry MB, Griffiths RJ, Sanganee MJ, Steel PG, Whelligan DK. Tetrahedron Lett. 2003; 44: 9135

• 116 Laub HA, Yamamoto H, Mayr H. Org. Lett. 2010; 12: 5206

• 117 Jones NR, Pattenden G. Tetrahedron Lett. 2009; 50: 3527

• 118 Barata-Vallejo S, Postigo A. J. Org. Chem. 2010; 75: 6141

• 119 Wang Z, Pitteloud J.-P, Montes L, Rapp M, Derane D, Wnuk SF. Tetrahedron 2008; 64: 5322

• 120 Ishida N, Ikemoto W, Murakami M. Org. Lett. 2012; 14: 3230

• 121 Rouquet G, Robert F, Méreau R, Castet F, Renaud P, Landais Y. Chem.–Eur. J. 2012; 18: 940

• 122 Gilman H, Inoue S. J. Org. Chem. 1964; 29: 3418

• 123 Gilges H, Kickelbick G, Schubert U. J. Organomet. Chem. 1997; 548: 57

• 124 Gaspar PP, West R, In: The Chemistry of Organic Silicon Compounds Rappoport Z, Apeloig Y. Wiley Chichester, UK 1998; 2. 2463

• 125 Lambert JB, Pflug JL, Denari JM. Organometallics 1996; 15: 615

• 126 Gilman H, Smith CL. J. Organomet. Chem. 1968; 14: 91

• 127 Klinkhammer KW, Schwarz W. Z. Anorg. Allg. Chem. 1993; 619: 1777

• 128 Marschner C. Eur. J. Inorg. Chem. 1998; 221

• 129 Kayser C, Fischer R, Baumgartner J, Marschner C. Organometallics 2002; 21: 1023

• 130 Niemeyer M. Inorg. Chem. 2006; 45: 9085

• 131 Krempner C, Reinke H, Oehme H. Angew. Chem. 1994; 106: 1709 Angew. Chem. Int. Ed. Engl. 1994; 33: 1615

• 132 Farwell JD, Lappert MF, Marschner C, Strissel C, Tilley TD. J. Organomet. Chem. 2000; 603: 185

• 133 Gaderbauer W, Zirngast M, Baumgartner J, Marschner C, Tilley TD. Organometallics 2006; 25: 2599

• 134 Bürger H, Kilian W, Burczyk K. J. Organomet. Chem. 1970; 21: 291

• 135 Bochmann M, Green MLH, Powell AK, Saßmannshausen J, Triller MU, Wocadlo S. J. Chem. Soc., Dalton Trans. 1999; 43

• 136 Mechtler C, Marschner C. Tetrahedron Lett. 1999; 40: 7777

• 137 Wallner A, Hlina J, Wagner H, Baumgartner J, Marschner C. Organometallics 2011; 30: 3930

• 138 Fischer R Ph.D. Dissertation, TU Graz 2003

• 139 Apeloig Y, Bendikov M, Yuzefovich M, Nakash M, Bravo-Zhivotovskii D, Bläser D, Boese R. J. Am. Chem. Soc. 1996; 118: 12 228

• 140 Wendler C, Oehme H. Z. Anorg. Allg. Chem. 1996; 622: 801

• 141 Hoffmann D, Gross T, Kempe R, Oehme H. J. Organomet. Chem. 2000; 598: 395

• 142 Schmohl K, Blach M, Reinke H, Kempe R, Oehme H. Eur. J. Inorg. Chem. 1998; 1667

• 143 Gilman H, Shiina K. J. Organomet. Chem. 1967; 8: 369

• 144 Larson GL. PharmaChem 2010; 9: 26

• 145 Sore HF, Galloway WRJD, Spring DR. Chem. Soc. Rev. 2012; 41: 1845

• 146 Hiyama T. J. Organomet. Chem. 2002; 653: 58

• 147 Wnuk SF, Garcia Jr PI, Wang Z. Org. Lett. 2004; 6: 2047

• 148 Yamanoi Y. J. Org. Chem. 2005; 70: 9607

• 149 Yamanoi Y, Nishihara H. J. Org. Chem. 2008; 73: 6671

• 150 Hamze A, Provot O, Alami M, Brion J.-D. Org. Lett. 2006; 8: 931

• 151 Yamanoi Y, Taira T, Sato J.-i, Nakamula I, Nishihara H. Org. Lett. 2007; 9: 4543

• 152 Murata M, Watanabe S, Masuda Y. Tetrahedron Lett. 1999; 40: 9255

• 153 Yamanoi Y, Nishihara H. Tetrahedron Lett. 2006; 47: 7157

• 154 Karshtedt D, Bell AT, Tilley TD. Organometallics 2006; 25: 4471

• 155 Miura K, Oshima K, Utimoto K. Bull. Chem. Soc. Jpn. 1993; 66: 2356

• 156 Liu Y, Yamazaki S, Yamabe S. J. Org. Chem. 2005; 70: 556

• 157 Wuts PGM, Greene TW. Greene’s Protective Groups in Organic Synthesis. Wiley-Interscience; Hoboken, NJ 2006

• 158 Kocieński PJ. Protecting Groups. Thieme; Stuttgart 2005

• 159 Guliashvili T, Tibbelin J, Ryu J, Ottosson H. Dalton Trans. 2010; 39: 9379

• 160 Al-Juaid SS, Derouiche Y, Hitchcock PB, Lickiss PD, Brook AG. J. Organomet. Chem. 1991; 403: 293

• 161 El-Sayed I, Guliashvili T, Hazell R, Gogoll A, Ottosson H. Org. Lett. 2002; 4: 1915

• 162 Fischer R, Baumgartner J, Kickelbick G, Hassler K, Marschner C. Monatsh. Chem. 2006; 137: 613

• 163 Fischer R, Baumgartner J, Kickelbick G, Hassler K, Marschner C. Chem.–Eur. J. 2004; 10: 1021