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A mild and efficient cyanosilylation of ketones catalyzed by a Lewis acid–Lewis base bifunctional catalyst

✍ Scribed by Yongcun Shen; Xiaoming Feng; Yan Li; Guolin Zhang; Yaozhong Jiang

Book ID
104205533
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
204 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

A new family of bifunctional catalysts (N-oxides -Ti(O i Pr) 4 (2:1)) containing a Lewis acid and a Lewis base was developed and applied to the catalytic cyanosilylation of ketones. Utilizing rac((1R,2S) and (1S,2R))-1-(2 0 -pyridylmethyl)-2-diphenylhydroxymethylpyrrolidine N-oxide -titanium (2:1) complex and N-benzyl-diethanolamine N-oxide -titanium (2:1) complex as catalysts, the cyanosilylation products were obtained in 42 -97% yield. Based on experimental phenomena and kinetic studies, a catalytic cycle was proposed to explain the remarkable activities of these catalysts. Investigations indicated that rac((1R,2S) and (1S,2R))-1-(2 0 -pyridylmethyl)-2-diphenylhydroxymethylpyrrolidine N-oxide -titanium (2:1) complex and N-benzyl-diethanolamine N-oxide -titanium (2:1) complex should promote the reaction via a dual activation of the ketone by the titanium and TMSCN by the N-oxide.

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