Synthesis 2019; 51(17): 3305-3312
DOI: 10.1055/s-0037-1611824
paper
© Georg Thieme Verlag Stuttgart · New York

New Zinc Catalyst for Hydrosilylation of Carbonyl Compounds

Iryna D. Alshakova
,
Brock University, 1812 Sir Isaac Brock Way, St. Catharines, ON, L2S 3A1, Canada   Email: gnikonov@brocku.ca
› Author Affiliations
This research was supported by the Natural Sciences and Engineering Research Council of Canada (Discovery Grant, 2017-05231 to G.I.N.).
Further Information

Publication History

Received: 07 March 2019

Accepted after revision: 18 April 2019

Publication Date:
07 May 2019 (online)


Abstract

A new zinc complex was synthesized and applied in the catalytic hydrosilylation of carbonyl compounds. Optimization of the reaction conditions showed that the presence a substoichiometric amount of methanol accelerates the process significantly. The reaction can proceed at very low catalyst load (down to 0.1 mol%) under mild reaction conditions. The reaction tolerates the presence of C=C bonds, and thus can be useful for the synthesis of allylic alcohols from α,β-unsaturated aldehydes and ketones.

Supporting Information

 
  • References

  • 1 Díez-González S, Nolan SP. Org. Prep. Proced. Int. 2007; 39: 523
    • 3a Szwarc-Rzepka K, Ciesielczyk F, Jesionowski T. J. Nanomater. 2013; 674237
    • 3b Trewyn BG, Slowing II, Giri S, Chen HT, Lin VS. Y. Acc. Chem. Res. 2007; 40: 846
    • 4a Wei YF, Liu SX, Mueller-Bunz H, Albrecht M. ACS Catal. 2016; 6: 8192
    • 4b Nguyen TV. Q, Yoo WJ, Kobayashi S. Adv. Synth. Catal. 2016; 358: 452
    • 4c Zuo ZQ, Zhang L, Leng XB, Huang Z. Chem. Commun. 2015; 51: 5073
    • 4d Huckaba AJ, Hollis TK, Reilly SW. Organometallics 2013; 32: 6248
    • 4e Peterson E, Khalimon AY, Simionescu R, Kuzmina LG, Howard JA. K, Nikonov GI. J. Am. Chem. Soc. 2009; 131: 908
    • 4f Riener K, Hogerl MP, Gigler P, Kuhn FE. ACS Catal. 2012; 2: 613
    • 4g Chatterjee B, Gunanathan C. Chem. Commun. 2014; 50: 888
    • 6a Calas R. Pure Appl. Chem. 1966; 13: 61
    • 6b Calas R, Frainnet E, Bazouin A. C. R. Hebd. Seances Acad Sci. 1962; 254: 2357
    • 6c Calas R, Frainnet E, Bazouin A. C. R. Hebd. Seances Acad Sci. 1961; 252: 420
    • 6d Calas R, Frainnet E, Bazouin A. C. R. Hebd. Seances Acad Sci. 1963; 257: 1304
    • 6e Calas R, Frainnet E, Berthault A. C. R. Hebd. Seances Acad Sci. 1964; 258: 613
  • 7 Ohkuma T, Hashiguchi S, Noyori R. J. Org. Chem. 1994; 59: 217
  • 8 Mimoun H. J. Org. Chem. 1999; 64: 2582
    • 9a Bette V, Mortreux A, Savoia D, Carpentier JF. Adv. Synth. Catal. 2005; 347: 289
    • 9b Bette V, Mortreux A, Lehmann CW, Carpentier JF. Chem. Commun. 2003; 332
    • 9c Bette V, Mortreux A, Ferioli F, Martelli G, Savoia D, Carpentier JF. Eur. J. Org. Chem. 2004; 3040
    • 10a Mastranzo VM, Quintero L, de Parrodi CA, Juaristi E, Walsh PJ. Tetrahedron 2004; 60: 1781
    • 10b Ushio H, Mikami K. Tetrahedron Lett. 2005; 46: 2903
    • 10c Inagaki T, Yamada Y, Phong LT, Furuta A, Ito JI, Nishiyama H. Synlett 2009; 253
    • 10d Santacruz E, Huelgas G, Angulo SK, Mastranzo VM, Hernández-Ortega S, Aviña JA, Juaristi E, de Parrodi CA, Walsh PJ. Tetrahedron: Asymmetry 2009; 20: 2788
    • 10e Roh SG, Yoon JU, Jeong JH. Polyhedron 2004; 23: 2063
    • 10f Szewczyk M, Bezłada A, Mlynarski J. ChemCatChem 2016; 8: 3575
  • 11 Kahnes M, Görls H, González L, Westerhausen M. Organometallics 2010; 29: 3098
  • 12 Marinos NA, Enthaler S, Driess M. ChemCatChem 2010; 2: 846
  • 13 Enthaler S, Schröder K, Inoue S, Eckhardt B, Junge K, Beller M, Driess M. Eur. J. Org. Chem. 2010; 4893
  • 14 Boone C, Korobkov I, Nikonov GI. ACS Catal. 2013; 3: 2336
  • 15 Mou ZH, Xie HY, Wang MY, Liu N, Yao CG, Li L, Liu JY, Li SH, Cui DM. Organometallics 2015; 34: 3944
  • 16 Lummis PA, Momeni MR, Lui MW, McDonald R, Ferguson MJ, Miskolzie M, Brown A, Rivard E. Angew. Chem. Int. Ed. 2014; 53: 9347
  • 17 Rit A, Zanardi A, Spaniol TP, Maron L, Okuda J. Angew. Chem. Int. Ed. 2014; 53: 13273
  • 18 Sattler W, Ruccolo S, Chaijan MR, Allah TN, Parkin G. Organometallics 2015; 34: 4717
  • 19 Dawkins MJ. C, Middleton E, Kefalidis CE, Dange D, Juckel MM, Maron L, Jones C. Chem. Commun. 2016; 52: 10490
    • 20a Valdés H, García-Eleno MA, Canseco-Gonzalez D, Morales-Morales D. ChemCatChem 2018; 10: 3136
    • 20b Grützmacher H. Angew. Chem. Int. Ed. 2008; 47: 1814
  • 21 Jozak T, Zabel D, Schubert A, Sun Y, Thiel WR. Eur. J. Inorg. Chem. 2010; 5135
  • 22 Maret W. Biochemistry 2004; 43: 3301
  • 23 Mukherjee D, Thompson RR, Ellern A, Sadow AD. ACS Catal. 2011; 1: 698
  • 24 Haack KJ, Hashiguchi S, Fujii A, Ikariya T, Noyori R. Angew. Chem. Int. Ed. 1997; 36: 285
    • 25a Dub PA, Henson NJ, Martin RL, Gordon JC. J. Am. Chem. Soc. 2014; 136: 3505
    • 25b Dub PA, Gordon JC. ACS Catal. 2017; 7: 6635