Download PDF
Cazin, C.  et al.: 2017 Science of Synthesis, 2016/5a: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1 DOI: 10.1055/sos-SD-223-00160
N-Heterocyclic Carbenes in Catalytic Organic Synthesis

1.4.3 Hydrosilylation

More Information

Book

Editors: Cazin, C. ; Nolan, S.

Authors: Albrecht, M.; Baudrenghien, L.; Bielawski, C.; Biffis, A.; Cavallo, L.; Cazin, C. ; César, V.; Chetcuti, M.; Cuenca, A.; de Frémont, P.; Elie, M.; Fairlamb, I.; Falivene, L.; Fernandez Gutierrez, M. E.; Gagné, M. R.; Gaillard, S.; Huynh, H.; Kalck, P.; Kuwano, R.; Lastovickova, D.; Lavigne, G.; Makida, Y.; Marko, I.; Martin, A.; Nahra, F. ; Nakao, Y.; Ogasawara, M. ; Payne, P.; Renaud, J.; Ronson, T.; Ruamps, M.; Segarra Almela, C.; Teator, A.; Trzeciak, A.; Tubaro, C.; Urrutigoity, M.; Vummaleti, S.; Whittlesey, M.; Yuan, D.

Title: N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1

Print ISBN: 9783132012813; Online ISBN: 9783132407633; Book DOI: 10.1055/b-004-132254

1st edition © 2017. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

Also available at
 


Abstract

Hydrosilylation of alkenes and alkynes, promoted by various generations of now commercially available (or easily formed) platinum–N-heterocyclic carbene complexes, enables efficient access to valuable silanes. Under optimal conditions, this process constitutes an atom economical, solvent-free, green process yielding terminal alkylsilanes and β-(E)-vinylsilanes in a rapid, efficient, and selective manner.

Key words

N-heterocyclic carbenes - hydrosilylation - alkenes - alkynes - alkylsilanes - vinylsilanes - platinum - siloxanes
 
  • 1 Sommer, LH, Pietrusza, EW, Whitmore, FC. J. Am. Chem. Soc.. 1947; 69: 188
    Google Scholar
  • 2 Hydrosilylation: A Comprehensive Review on Recent Advances. Marciniec, BED. Springer; New York 2009
    Google Scholar
  • 4 Troegel, D, Stohrer, J. Coord. Chem. Rev.. 2011; 255: 1440
    Google Scholar
  • 6 Rösch, L, John, P, Reitmeier, R. In Ullmannʼs Encyclopedia of Industrial Chemistry. 5th ed.. Wiley-VCH; Weinheim, Germany 2000. Vol. A24.
    Google Scholar
  • 7 Armitage, DA, In Comprehensive Organometallic Chemistry. Wilkinson, G, Stone, FGA, Abel, EW, Eds;. Pergamon; Oxford 1982. Vol. 2, 117.
    Google Scholar
  • 9 Karstedt, BD. US 3715334, 1973
  • 10 Hitchcock, PB, Lappert, MF, Warhurst, NJW. Angew. Chem. Int. Ed. Engl.. 1991; 30: 438
    Google Scholar
  • 11 Lewis, LN, Stein, J, Gao, Y, Colborn, RE, Hutchins, G. Platinum Met. Rev.. 1997; 41: 66
    Google Scholar
  • 12 Chalk, AJ, Harrod, JF. J. Am. Chem. Soc.. 1965; 87: 16
    Google Scholar
  • 13 Dierick, S, Vercruysse, E, Berthon-Gelloz, G, Markó, IE. Chem.–Eur. J.. 2015; 21: 17073
    Google Scholar
  • 14 Stein, J, Lewis, LN, Gao, Y, Scott, RA. J. Am. Chem. Soc.. 1999; 121: 3693
    Google Scholar
  • 15 Sprengers, JW, Mars, MJ, Duin, MA, Cavell, KJ, Elsevier, CJ. J. Organomet. Chem.. 2003; 679: 149
    Google Scholar
  • 16 Sprengers, JW, de Greef, M, Duin, MA, Elsevier, CJ. Eur. J. Inorg. Chem.. 2003; 3811
    Google Scholar
  • 17 Sprengers, JW, Agerbeek, MJ, Elsevier, CJ, Kooijman, H, Spek, AL. Organometallics. 2004; 23: 3117
    Google Scholar
  • 18 Dierick, S, Markó, IE, In N-Heterocyclic Carbenes: Effective Tools for Organometallic Synthesis. Nolan, SP, ED. Wiley-VCH Weinheim, Germany 2014; p 111
    Google Scholar
  • 19 Markó, IE, Stérin, S, Buisine, O, Mignani, G, Branlard, P, Tinant, B, Declercq, J.-P. Science (Washington, D. C.). 2002; 298: 204
    Google Scholar
  • 20 Scott, NM, Nolan, SP. Eur. J. Inorg. Chem.. 2005; 1815
    Google Scholar
  • 21 Markó, IE, Stérin, S, Buisine, O, Berthon, G, Michaud, G, Tinant, B, Declercq, J.-P. Adv. Synth. Catal.. 2004; 346: 1429
    Google Scholar
  • 22 Buisine, O, Berthon-Gelloz, G, Brière, J.-F, Stérin, S, Mignani, G, Branlard, P, Tinant, B, Declercq, J.-P, Markó, IE. Chem. Commun. (Cambridge). 2005; 3856
    Google Scholar
  • 23 Berthon-Gelloz, G, Buisine, O, Brière, J.-F, Michaud, G, Stérin, S, Mignani, G, Tinant, B, Declercq, J.-P, Chapon, D, Markó, IE. J. Organomet. Chem.. 2005; 690: 6156
    Google Scholar
  • 24 De Bo, G, Berthon-Gelloz, G, Tinant, B, Markó, IE. Organometallics. 2006; 25: 1881
    Google Scholar
  • 25 Böhm, VPW, Herrmann, WA. Angew. Chem. Int. Ed.. 2000; 39: 4036
    Google Scholar
  • 26 Berthon-Gelloz, G, Schumers, J.-M, Lucaccioni, F, Tinant, B, Wouters, J, Markó, IE. Organometallics. 2007; 26: 5731
    Google Scholar
  • 27 Berthon-Gelloz, G, Schumers, J.-M, De Bo, G, Markó, IE. J. Org. Chem.. 2008; 73: 4190
    Google Scholar
  • 28 Krause, J, Haack, K.-J, Cestaric, G, Goddard, R, Pörschke, K.-R. Chem. Commun. (Cambridge). 1998; 1291
    Google Scholar
  • 29 Lewis, LN, Colborn, RE, Grade, H, Bruyant, Jr. GL, Sumpter, CA, Scott, RA. Organometallics. 1995; 14: 2202
    Google Scholar
  • 30 Berthon-Gelloz, G, de Bruin, B, Tinant, B, Markó, IE. Angew. Chem. Int. Ed.. 2009; 48: 3161
    Google Scholar
  • 32 Trost, BM, Ball, ZT. J. Am. Chem. Soc.. 2001; 123: 12726
    Google Scholar
  • 33 Trost, BM, Ball, ZT. J. Am. Chem. Soc.. 2005; 127: 17644
    Google Scholar
  • 34 Ojima, I, Clos, N, Donovan, RJ, Ingallina, P. Organometallics. 1990; 9: 3127
    Google Scholar
  • 35 Doyle, MP, High, KG, Nesloney, CL, Clayton, Jr. TW, Lin, J. Organometallics. 1991; 10: 1225
    Google Scholar
  • 37 Mori, A, Takahisa, E, Yamamura, Y, Kato, T, Mudalige, AP, Kajiro, H, Hirabayashi, K, Nishihara, Y, Hiyama, T. Organometallics. 2004; 23: 1755
    Google Scholar
  • 38 Green, M, Spencer, JL, Stone, FGA, Tsipis, CA. J. Chem. Soc., Dalton Trans.. 1977; 1525
    Google Scholar
  • 39 Huang, J, Schanz, H.-J, Stevens, ED, Nolan, SP. Organometallics. 1999; 18: 2370
    Google Scholar
  • 40 Viciu, MS, Navarro, O, Germaneau, RF, Kelly, III RA, Sommer, W, Marion, N, Stevens, ED, Cavallo, L, Nolan, SP. Organometallics. 2004; 23: 1629
    Google Scholar