Tris(pentafluorophenyl)silyl Triflate: Synthesis and Silylation of Carbonyl Compounds

Tris(pentafluorophenyl)silyl Triflate: Synthesis and Silylation of Carbonyl Compounds Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2004, Volume: 2004, Number: 24, Pages: 5141-5148 Pages count : 8 DOI: 10.1002/ejoc.200400552

Authors

Levin Vitalij V. ¹ , Dilman Alexander D. ¹ , Belyakov Pavel A. ¹ , Korlyukov Alexander A. ² , Struchkova Marina I. ¹ , Tartakovsky Vladimir A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry 119991 Moscow, Leninsky prosp. 47, Russian Federation, Fax: +7-095-135-5328
2	A. N. Nesmeyanov Institute of Organoelement Compounds, 119991 Moscow, Vavilov str. 28, Russian Federation

Tris(pentafluorophenyl)silyl triflate (1) was prepared by protodesilylation of phenyl-, allyl-, and isopropenyloxytris(pentafluorophenyl)silyl derivatives and characterized by X-ray crystallography. This reagent was employed for the silylation of carbonyl compounds. Aldehydes and ketones afforded the corresponding silyl enol ethers in good yields, while silylation of esters and lactones was dependent on the reaction conditions and on the substrate. A mechanism accounting for the observed phenomena is proposed. Studies of the relative reactivities of 1 and trimethylsilyl triflate are also presented.

Levin V. , Dilman A. , Belyakov P. , Korlyukov A. , Struchkova M. , Tartakovsky V.
Tris(pentafluorophenyl)silyl Triflate: Synthesis and Silylation of Carbonyl Compounds
European Journal of Organic Chemistry. 2004. V.2004. N24. P.5141-5148. DOI: 10.1002/ejoc.200400552 WOS Scopus OpenAlex

Web of science:	WOS:000225858100024
Scopus:	2-s2.0-11144319356
OpenAlex:	W2154694911

DB	Citing
OpenAlex	14
Scopus	13
Web of science	12