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

被引：116

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.

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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 [J].

Adhikari, Debashis ;

Mossin, Susanne ;

Basuli, FaIguni ;

Huffman, John C. ;

Szilagyi, Robert K. ;

Meyer, Karsten ;

Mindiola, Daniel 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 [J].

Adhikari, Debashis ;

Huffman, John C. ;

Mindiola, Daniel 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 [J].

Adhikari, Debashis ;

Mossin, Susanne ;

Basuli, FaIguni ;

Dible, Benjamin R. ;

Chipara, Mircea ;

Fan, Hongjun ;

Huffman, John C. ;

Meyer, Karsten ;

Mindiola, Daniel 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 [J].

ARRIORTUA, MI ;

CORTES, AR ;

LEZAM, L ;

ROJO, T ;

SOLANS, X ;

FONTBARDIA, M .

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 [J].

Bach, I ;

Goddard, R ;

Kopiske, C ;

Seevogel, K ;

Pörschke, KR .

ORGANOMETALLICS, 1999, 18 (01) :10-20

[6] A β-diketiminato-nickel(II) synthon for nickel(I) complexes [J].

Bai, GC ;

Wei, PR ;

Stephan, DW .

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 [J].

Bailey, Brad C. ;

Tout, Alison R. ;

Fan, Hongjun ;

Tomaszewski, John ;

Huffman, John C. ;

Mindiola, Daniel J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (43) :8246-8249

[8] NICKEL COMPLEXES AS HYDROSILATION CATALYSTS [J].

BENNETT, EW ;

ORENSKI, PJ .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 28 (01) :137-&

[9] [Zinc-diamine]-catalyzed hydrosilylation of ketones in methanol. New developments and mechanistic insights [J].

Bette, V ;

Mortreux, A ;

Savoia, D ;

Carpentier, JF .

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 [J].

Bette, V ;

Mortreux, A ;

Ferioli, F ;

Martelli, G ;

Savoia, D ;

Carpentier, JF .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (14) :3040-3045

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