105304-62-9Relevant articles and documents
Effect of Fluorination on Skin Sensitization Potential and Fragrant Properties of Cinnamyl Compounds
Charpentier, Julie,Emter, Roger,Koch, Heinz,Lelièvre, Dominique,Pannecoucke, Xavier,Couve-Bonnaire, Samuel,Natsch, Andreas,Bombrun, Agnes
, (2018)
A series of three α- and three β-fluorinated representatives of the family of cinnamate-derived odorants (cinnamaldehyde (1), cinnamyl alcohol (2), and ethyl cinnamate (3)) as used as fragrance ingredients is described. Olfactive evaluation shows that the
N-heterocyclic carbene-catalysed Peterson olefination reaction
Wang, Ying,Du, Guang-Fen,Gu, Cheng-Zhi,Xing, Fen,Dai, Bin,He, Lin
, p. 472 - 478 (2016)
N-heterocyclic carbenes (NHCs) have been utilised as highly efficient organocatalysts to catalyse Peterson olefination reaction of aldehydes with trimethylsilylketene ethyl trimethylsilyl acetal or fluoro(trimethylsilyl)ketene ethyl trimethylsilyl acetal to produce the corresponding functionalized olefines in 34-93% yields with excellent stereoselectivities.
Heck reaction with ethyl (E)- and (Z)-3-fluoropropenoate
Patrick, Timothy B.,Blay, Angela A.
, p. 68 - 69 (2016)
The use of monofluoro alkene substrates in the Heck reaction is relatively unknown. The reaction between ethyl E-3-fluoropropenoate or ethyl Z-3-fluoropropenoate with iodobenzene and palladium acetate produces only ethyl 3-fluoropropenoate (Z-6). Some los
Enantioselective synthesis of β-fluoro-β-aryl-α-aminopentenamides by organocatalytic [2,3]-sigmatropic rearrangement
Kasten, Kevin,Slawin, Alexandra M. Z.,Smith, Andrew D.
, p. 5182 - 5185 (2017)
The tetramisole-promoted catalytic enantioselective [2,3]-sigmatropic rearrangement of quaternary ammonium salts bearing a (Z)-3-fluoro-3-arylprop-2-ene group generates, after addition of benzylamine, a range of β-fluoro-β-aryl-α-aminopentenamides containing a stereogenic tertiary fluorine substituent. Cyclic and acyclic nitrogen substituents as well as various aromatic substituents are tolerated, giving the β-fluoro-β-aryl-α-aminopentenamide products in up to 76% yield, 96:4 dr, and 98:2 er.
Gold N-Heterocyclic Carbene Catalysts for the Hydrofluorination of Alkynes Using Hydrofluoric Acid: Reaction Scope, Mechanistic Studies and the Tracking of Elusive Intermediates
Bédard, Sandrine,Cavallo, Luigi,Falivene, Laura,Gauthier, Rapha?l,Nolan, Steven P.,Paquin, Jean-Fran?ois,Saab, Marina,Tzouras, Nikolaos V.,Van Hecke, Kristof,Zhang, Ziyun
supporting information, (2021/12/09)
An efficient and chemoselective methodology deploying gold-N-heterocyclic carbene (NHC) complexes as catalysts in the hydrofluorination of terminal alkynes using aqueous HF has been developed. Mechanistic studies shed light on an in situ generated catalyst, formed by the reaction of Br?nsted basic gold pre-catalysts with HF in water, which exhibits the highest reactivity and chemoselectivity. The catalytic system has a wide alkyl substituted-substrate scope, and stoichiometric as well as catalytic reactions with tailor-designed gold pre-catalysts enable the identification of various gold species involved along the catalytic cycle. Computational studies aid in understanding the chemoselectivity observed through examination of key mechanistic steps for phosphine- and NHC-coordinated gold species bearing the triflate counterion and the elusive key complex bearing a bifluoride counterion.
A metal-free and regioselective approach to (Z)-β-fluorovinyl sulfones and their chemoselective hydrogenation to β-fluoroalkyl sulfones
Sedgwick, Daniel M.,Román, Raquel,Barrio, Pablo,Morales, Cristina,Fustero, Santos
, p. 108 - 116 (2018/01/01)
A highly regioselective, metal-free hydrofluorination reaction of alkynyl sulfones was developed using TBAF—one of the cheapest and most commonly available fluoride sources. In addition, the reactivity of the resulting β-fluorovinyl sulfones was studied, focusing on their selective hydrogenation reaction. Both β-fluorovinyl sulfones and their hydrogenation products β-fluoroalkyl sulfones may find applications in medicinal and agrochemical sciences.
