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1,4‐Diazabicyclo[2.2.2]octane Trifluoroacetate: A Highly Efficient Organocatalyst for the Cyanosilylation of Carbonyl Compounds under Solvent Free Condition
Author(s) -
Yadav Geeta Devi,
Singh Surendra
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700674
Subject(s) - trimethylsilyl cyanide , chemistry , dabco , octane , catalysis , aldehyde , organic chemistry , yield (engineering) , methanol , solvent , ketone , trimethylsilyl , medicinal chemistry , materials science , metallurgy
Salts of DABCO (1,4‐diazabicyclo[2.2.2]octane) were synthesised. The catalytic activities of these salts (0.125–1 mol%) were evaluated for cyanosilylation of various aldehydes and ketones under solvent‐free conditions using TMSCN (trimethylsilyl cyanide). Aldehydes were found to more reactive compared to the ketones and excellent yields of corresponding cyanosilylether were achieved within 5 min to 54 h. Cynaosilylation of aldehydes and ketones with electron withdrawing group found to be more reactive than the aldehydes and ketones bearing electron donating group. Silylcyanation of isatin and its derivatives was carried out and the corresponding products were obtained in 74‐90 % yields after 3–10 minutes. We also demonstrated that the catalyst could deprotect the TMS group of cyanosilylether in methanol in quantitative yield.