59888-13-0Relevant academic research and scientific papers
Copper(I)-Mediated Borofluorination of Alkynes
Jordan, Abraham J.,Thompson, Percie K.,Sadighi, Joseph P.
, p. 5242 - 5246 (2018/09/12)
The electrophilic fluorination of N-heterocyclic carbene (NHC) copper(I) vinyls results in fluoroalkene formation. Alkynes can be converted to cis-(β-fluorovinyl)boronates by a reaction with an (NHC)copper(I) boryl generated in situ, followed by N-fluorobenzenesulfonimide (NFSI). This sequence gives rise to anti-Markovnikov fluorination products from terminal alkynes. Oxidation of a cis-(β-fluorovinyl)trifluoroboronate yields an α-fluoroketone, whereas a palladium-catalyzed Suzuki-Miyaura coupling yields a tetrasubstituted monofluoroalkene.
Catalytic C-F bond activation of geminal difluorocyclopropanes by nickel(i) complexes via a radical mechanism
Wenz, Jan,Rettenmeier, Christoph A.,Wadepohl, Hubert,Gade, Lutz H.
supporting information, p. 202 - 205 (2015/12/26)
Nickel(ii) fluorido complexes bearing NNN-pincer ligands were found to be catalysts in the hydrodefluorination of geminal difluorocyclopropanes which undergo ring-opening to form the corresponding monofluoroalkenes in good yield and high Z-selectivities. Evidence for a radical based mechanism involving nickel(i) and nickel hydrido complexes as key intermediates was obtained in the corresponding stoichiometric reactions.
Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF3as an Additive
Ye, Yuxuan,Takada, Takashi,Buchwald, Stephen L.
, p. 15559 - 15563 (2016/12/09)
A method for the palladium-catalyzed fluorination of cyclic vinyl triflates has been developed. As with several previous palladium-catalyzed fluorination reactions using fluoride salts, controlling the regioselectivity presented a challenge in developing a practical synthetic procedure. The addition of triethyl(trifluoromethyl)silane (TESCF3) was found to effectively address this problem and resulted in drastically improved regioselectivities in this palladium-catalyzed fluorination reaction. This discovery, along with the use of a new biarylphosphine ligand, allowed for the development of an efficient and highly regioselective protocol for the fluorination of vinyl triflates. This method is compatible with a range of sensitive functional groups and provides access to five-, six-, and seven-membered cyclic vinyl fluorides.
A convenient one-step synthesis of fluoroethylidene derivatives
Chevrie,Lequeux,Demoute,Pazenok
, p. 8127 - 8130 (2007/10/03)
A convenient one-step synthesis of gem-monofluoroalkylolefins starting from aldehydes or ketones was developed. This method comprises the utilisation of 2-(1-fluoroethyl)sulfonyl-1,3-benzothiazole according to Julia's procedure and opens a new opportunity
Preparation of monofluoroalkenes
-
Example 6, (2008/06/13)
There is described a process for the preparation of compounds of formula I in whichR is hydrogen, optionally substituted alkyl, optionally substituted alkenyl optionally substituted cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclyl, andR1 and R2 are hydrogen, an organic radical or together with the ring to which they are attached, form an optionally substituted ring, which may contain one or more hetero atoms, which comprises reacting a compound of formula II with a compound of formula III in which the ring Q is an optionally substituted heteroaromatic ring, which optionally comprises one or more further hetero atoms and to which is optionally fused an optionally substituted ring.
Reaction of Chiral Cyclopropyl Halides with SmI2
Walborsky, H. M.,Topolski, Marek
, p. 370 - 373 (2007/10/02)
Reductions of (S)-(+)-1-bromo-1-methyl-2,2-diphenylcyclopropane (7), (S)-(+)-1-bromo-1-(methoxymethyl)-2,2-diphenylcyclopropane (19), and (R)-(-)-1-fluoro-1-iodo-2,2-diphenylcyclopropane (11) with samarium(II) iodide is reported.Evidence for a samarium(III) intermediate in the reaction is presented.
Formation of a Chiral 1-Fluoro-2,2-diphenylcyclopropyl Radical in the Barton Decarboxylation Reaction
Gawronska, K.,Gawronski, J.,Walborsky, H. M.
, p. 2193 - 2197 (2007/10/02)
The chiral 1-fluoro-2,2-diphenylcyclopropyl radical (8), generated in the Barton decarboxylation reaction, was used as a probe to evaluate a variety of halogen and hydrogen atom donating reagents as radical traps
