• Title/Summary/Keyword: TMSCN

Search Result 8, Processing Time 0.018 seconds

Phosphomolybdic Acid Supported on Silica Gel as an Efficient and Reusable Catalyst for Cyanosilylation of Aldehydes

  • Kadam, Santosh T.;Kim, Sung-Soo
    • Bulletin of the Korean Chemical Society
    • /
    • v.29 no.7
    • /
    • pp.1320-1322
    • /
    • 2008
  • Phosphomolybdic acid supported on silica gel (PMA-$SiO_2$) is an efficient catalyst for the activation of TMSCN for the facile cyanosilylation of various aldehydes. Cyano transfer from TMSCN to aldehyde proceeds smoothly at rt in presence of 0.8 mol % of PMA-$SiO_2$ leading to a range of cyanosilylether in excellent yield (mostly over 93%) within short reaction time (30 min). The catalyst can be recovered and reused several times without loss of activity.

Efficient, Rapid and Solvent-free Cyanosilylation of Aldehydes and Ketones Catalyzed by SbCl3

  • Pourmousavi, S.A.;Salahshornia, H.
    • Bulletin of the Korean Chemical Society
    • /
    • v.32 no.5
    • /
    • pp.1575-1578
    • /
    • 2011
  • Antimony trichloride (SbCl3) was demonstrated to be an effective catalyst for the cyanosilylation of a wide variety of carbonyl compounds under solvent-free conditions. The reactions proceeded smoothly at room temperature to afford the corresponding cyanosilylethers in good to excellent yields.

Asymmetric Cyanosilylation of Aldehydes by Chiral Ti-TADDOL Complex

  • Kim, Sung-Soo;Kwak, Ju-Myung;Rajagopal, Gurusamy
    • Bulletin of the Korean Chemical Society
    • /
    • v.27 no.10
    • /
    • pp.1638-1640
    • /
    • 2006
  • A variety of chiral cyanohydrins were readily prepared from aldehydes with TMSCN under the influence of chiral titanium complex formed in situ from $Ti(O^iPr)_4$/TADDOL(I) in the presence of $Ph_3PO$ as additive. The double activation method produces trimethylsilylethers in excellent yield (95%) with moderate enantiomeric excess.

Solvent-free Cyanosilylation of Carbonyl Compounds Catalyzed by NbCl5

  • Georgea, Soney C.;Kim, Sung-Soo
    • Bulletin of the Korean Chemical Society
    • /
    • v.28 no.7
    • /
    • pp.1167-1170
    • /
    • 2007
  • A simple and convenient method for the addition of TMSCN to carbonyl compounds is described. NbCl5 is found to possess a strong Lewis acid property to transform carbonyl compounds smoothly to the corresponding cyanosilylether in high yields (up to 99 %) in solvent- free conditions.

Mild and Efficient Silylcyanation of Aldehydes Catalyzed by Zirconium Complex

  • Kim, Sung-Soo;Lee, Jun-Tae;Song, Dae-Ho;Lee, Ik-Mo;Park, Sun-Young
    • Bulletin of the Korean Chemical Society
    • /
    • v.26 no.2
    • /
    • pp.265-267
    • /
    • 2005
  • An efficient method of addition of trimethylsilyl cyanide to aldehydes by employing a zirconium complex as the catalyst has been described. A variety of aromatic, aliphatic, cyclic and heterocyclic aldehydes has been converted into corresponding trimethylsilyl ethers in excellent yield within short reaction time.

A New Combined Source of "CN" from N,N-Dimethylformamide and Ammonia in the Palladium-Catalyzed Cyanation of Aryl C-H Bonds

  • Choi, Ji-Ho;Kim, Jin-Ho;Chang, Suk-Bok
    • Proceedings of the Korean Vacuum Society Conference
    • /
    • 2011.08a
    • /
    • pp.207-207
    • /
    • 2011
  • Aromatic nitriles possess versatile utilities and are indispensible not only in organic synthesis but also in chemical industry. In fact, the nitrile group is an important precursor for various functional groups such as aldehydes, amines, amidines, tetrazoles, amides, and their carboxyl derivatives. Representative methods for the preparation of organonitriles with cyanide-containing reagents are the Sandmeyer and Rosenmund-von Braun reactions. Recently, a catalytic route to aryl nitriles has been reported on the basis of the chelation-assisted C-H bond activation or metal-catalyzed cyanation of haloarenes. In those cyanation protocols, the "CN" unit is provided from metal-bound precursors of MCN (M=Cu, K, Na, Zn), TMSCN, or K3Fe(CN)6. Additionally, it can be generated in situ from nitromethane or acetone cyanohydrin. Herein, we report the first example of generating "CN" from two different, readily available precursors, ammonia and N,N-dimethylformamide (DMF). In addition, its synthetic utility is demonstrated through the Pd-catalyzed cyanation of arene C-H bonds.

  • PDF