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A mild and efficient cyanosilylation of ketones catalyzed by a Lewis acid-Lewis base bifunctional catalyst |
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| Authors: | Yongcun ShenXiaoming Feng Yan LiGuolin Zhang Yaozhong Jiang |
| Institution: | a Sichuan Key Laboratory of Green Chemistry and Technology, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China b Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China c Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China |
| Abstract: | A new family of bifunctional catalysts (N-oxides-Ti(OiPr)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′-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′-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. |
| Keywords: | Lewis acid Lewis base catalyst cyanosilylation ketone |
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