Utilization of Tetrabutylammonium Triphenylsilyldifluoride as a Fluoride Source for Nucleophilic Fluorination

Nucleophilic trifluoromethylation of carbonyl compounds and derivatives

“…63 The reactivity and stereoselectivity of the reaction are dependent on the fluoride source. Thus, chiral sulfinyl imines 85 reacted with 1 (RPr) in the presence of 9 (TBAT) 64 in THF to give high diastereoselectivities and yields of the trifluoromethylated products 86, which can be hydrolyzed to the chiral amine salts 87 with high enantioselectivities (Scheme 40). The same group extended the method to the asymmetric synthesis of trifluoromethylated allylic amines 65 and vicinal ethylenediamines.…”

Syntheses of Precursors and Reference Compounds of the Melanin-Concentrating Hormone Receptor 1 (MCHR1) Tracers [11C]SNAP-7941 and [18F]FE@SNAP for Positron Emission Tomography

“…Unfortunately, different fluorination methods such as reactions with tetrabutylammonium fluoride [30], crown ether Kryptofix® K2.2.2 and potassium fluoride [34], or tetrabutylammonium-(triphenylsilyl) difluorosilicate [35] were unsuccessful. Minor yields of 4 (2%-3%) could be obtained by fluorination with cesium fluoride [36] and tetrabutylammoniumhydrogen difluoride [37].…”

Synthesis of Bioactive Natural Products as Protein Inhibitors

“…Prior to total synthesis of miraziridine A, three necessary unusual amino acids, EtO-Azd-OH, Fmoc-Sta-OH, and H-vArg-OEt, were synthesized. A hypervalent silicate reagents 17,18) TBAF/ TMSCN or TBAF/TMSN 3 , for the mild ring-opening reaction was employed as a key step in these routes. 19) Coupling of H-vArg-OEt with EtO-Azd-Leu-Sta-Abu-OH prepared by Fmoc-based SPPS was achieved by HATU/HOAt to give miraziridine A diethyl ester.…”