Catalytic Hydrosilylation of the Carbonyl Functionality via a Transient Nickel Hydride Complex

被引：115
作者：
Tran, Ba L. [1 ]
Pink, Maren [1 ]
Mindiola, Daniel J. [1 ]
机构：
[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
来源：
ORGANOMETALLICS | 2009年 / 28卷 / 07期
关键词：
H OXIDATIVE ADDITION; ASYMMETRIC HYDROSILYLATION; ENANTIOSELECTIVE HYDROSILYLATION; HOMOGENEOUS CATALYSIS; ALPHA; BETA-UNSATURATED KETONES; SILICON HYDRIDES; REDUCTION; LIGANDS; ALKYL; HYDROSILATION;
D O I：
10.1021/om801160j
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
We report the syntheses and characterization of two new sterically demanding chelate ligands, denoted PNMe3 (N-(2-(diisopropylphosphino)-4-methylphenyl)-2,4,6-trimethylanilide) and PNiPr3 (N-(2-(diisopropylphosphino)-4-methylphenyl)-2,4,6-triisopropylanilide), as well as the preparation of their nickel(II) halide complexes [(PNiPr3)Ni(mu(2)-Br)](2) (1) and [(PNMe3)Ni(mu(2)-Cl)](2) (2). The combination of complex 1 with (KOBu)-Bu-t and Et3SiH as the hydride source can promote the hydrosilylation of a variety of carbonyl compounds in excellent yield and in a catalytic manner. The reactivity for a scope of substrates and a plausible mechanism along the hydrosilylation reaction are discussed in this work.
引用
收藏
页码：2234 / 2243
页数：10
相关论文
共 93 条
  • [1] Structural, spectroscopic, and theoretical elucidation of a redox-active pincer-type ancillary applied in catalysis
    Adhikari, Debashis
    Mossin, Susanne
    Basuli, FaIguni
    Huffman, John C.
    Szilagyi, Robert K.
    Meyer, Karsten
    Mindiola, Daniel J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) : 3676 - 3682
  • [2] Structural elucidation of a nickel boryl complex. A recyclable borylation Ni(II) reagent of bromobenzene
    Adhikari, Debashis
    Huffman, John C.
    Mindiola, Daniel J.
    [J]. CHEMICAL COMMUNICATIONS, 2007, (43) : 4489 - 4491
  • [3] A Dinuclear Ni(I) System Having a Diradical Ni2N2 Diamond Core Resting State: Synthetic, Structural, Spectroscopic Elucidation, and Reductive Bond Splitting Reactions
    Adhikari, Debashis
    Mossin, Susanne
    Basuli, FaIguni
    Dible, Benjamin R.
    Chipara, Mircea
    Fan, Hongjun
    Huffman, John C.
    Meyer, Karsten
    Mindiola, Daniel J.
    [J]. INORGANIC CHEMISTRY, 2008, 47 (22) : 10479 - 10490
  • [4] CRYSTAL-STRUCTURE AND MAGNETIC-PROPERTIES OF [NI(TERPY)(N3)2]2.2H2O,A NICKEL(II) DINUCLEAR COMPLEX WITH FERROMAGNETIC INTERACTION
    ARRIORTUA, MI
    CORTES, AR
    LEZAM, L
    ROJO, T
    SOLANS, X
    FONTBARDIA, M
    [J]. INORGANICA CHIMICA ACTA, 1990, 174 (02) : 263 - 269
  • [5] Synthesis, structure, and reactivity of (tBu2PC2H4PtBu2)Ni(CH3)2 and {(tBu2PC2H4PtBu2)Ni}2(μ-H)2
    Bach, I
    Goddard, R
    Kopiske, C
    Seevogel, K
    Pörschke, KR
    [J]. ORGANOMETALLICS, 1999, 18 (01) : 10 - 20
  • [6] A β-diketiminato-nickel(II) synthon for nickel(I) complexes
    Bai, GC
    Wei, PR
    Stephan, DW
    [J]. ORGANOMETALLICS, 2005, 24 (24) : 5901 - 5908
  • [7] An alkylidyne analogue of tebbe's reagent: Trapping reactions of a titanium neopentylidyne by incomplete and complete 1,2-additions
    Bailey, Brad C.
    Tout, Alison R.
    Fan, Hongjun
    Tomaszewski, John
    Huffman, John C.
    Mindiola, Daniel J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (43) : 8246 - 8249
  • [8] NICKEL COMPLEXES AS HYDROSILATION CATALYSTS
    BENNETT, EW
    ORENSKI, PJ
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 28 (01) : 137 - &
  • [9] [Zinc-diamine]-catalyzed hydrosilylation of ketones in methanol. New developments and mechanistic insights
    Bette, V
    Mortreux, A
    Savoia, D
    Carpentier, JF
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) : 289 - 302
  • [10] New chiral 1,2-diamines and their use in zinc-catalyzed asymmetric hydrosilylation of acetophenone
    Bette, V
    Mortreux, A
    Ferioli, F
    Martelli, G
    Savoia, D
    Carpentier, JF
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (14) : 3040 - 3045
12345678910