Mild and Efficient Silylcyanation of Ketones Catalyzed by N-Methylmorpholine N-Oxide
Sung Soo Kim*, Dong Won Kim, Gurusamy Rajagopal
*Department of Chemistry and Center for Chemical Dynamics, Inha University,
Incheon 402-751, South Korea, Email: sungsoo
inha.ac.kr
S. S. Kim, D. W. Kim, G. Rajagopal, Synthesis, 2004, 213-216.
DOI: 10.1055/s-2003-44380
Abstract
An efficient method for achiral addition of TMSCN to ketones employs N-methylmorpholine N-oxide as catalyst. A variety of aromatic, aliphatic, cyclic and heterocyclic ketones are converted into their corresponding trimethylsilyl ethers in excellent yields.
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Details
The document describes a novel and efficient method for the silylcyanation of ketones using N-methylmorpholine N-oxide (NMO) as the sole catalyst. This method involves the addition of trimethylsilyl cyanide (TMSCN) to various ketones, resulting in the formation of trimethylsilyl ethers with excellent yields (>90%). The process is notable for its mild conditions, shorter reaction times, and the use of an inexpensive and readily available catalyst. The study highlights the versatility of NMO in activating both the ketone and TMSCN, facilitating the formation of cyanohydrins, which are valuable intermediates in the synthesis of various compounds, including pharmaceuticals and insecticides. The method has been successfully applied to a wide range of aromatic, aliphatic, cyclic, and heterocyclic ketones, demonstrating its broad applicability. The document also compares this method with other catalytic systems, emphasizing the advantages of using NMO alone, such as higher yields and shorter reaction times without the need for metal catalysts. The research suggests potential for further development into asymmetric versions of the reaction, enhancing its utility in synthetic chemistry.
Niobium Fluoride (NbF5): A Highly Efficient Catalyst for Solvent-Free Cyanosilylation of Aldehydes
S. S. Kim, G. Rajagopal, Synthesis, 2007, 215-218.
Key Words
silylcyanation, NMO, TMSCN, ketone, cyanohydrins
ID: J66-Y2004-1930
