98611-91-7Relevant academic research and scientific papers
Palladium-Catalyzed cascade sp2 c?H bond functionalizations allowing one-Pot access to 4?Aryl-1,2,3,4-tetrahydroquinolines from n?Allyl?N?arylsulfonamides
Yuan, Kedong,Soule, Jean-Francois,Dorcet, Vincent,Doucet, Henri
, p. 8121 - 8126 (2018/05/23)
We have developed a palladium-catalyzed cascade reaction allowing an efficient synthesis of 4-aryl-1,2,3,4-tetrahydroquinolines from N-allyl-N-arylsulfonamides and benzenesulfonyl chlorides. In this transformation, two C(sp2)?C(sp3) bonds were formed via activation of C(sp2)?H bonds. The reaction proceeds using the easily accessible catalyst PdCl2, with Li2CO3 as inexpensive base and CuBr as additive, and tolerates a wide variety of substituents on both reaction partners.
Fluorination of Aromatic Derivatives with Fluoroxytrifluoromethane and Bis(fluoroxy)difluoromethane
Fifolt, Michael J.,Olczak, Raymond T.,Mundhenke, Rudolph F.
, p. 4576 - 4582 (2007/10/02)
Fluoroxytrifluoromethane (CF3OF) and bis(fluoroxy)difluoromethane CF2(OF)2 are formed by the reaction of F2 with CO and CO2, respectively, over a CsF catalyst in a continouous-stream process.Both reagents react with aromatic substrates by an electrophilic substitution mechanism to yield fluoro-substituted derivatives.Fluorobenzene is produced in good yield from benzene, and aniline derivatives afford monofluorination products.Acetanilide (1), N-phenylmethanesulfonamide (2), α,α,α-trifluoroacetanilide (3), and 1,1,1-trifluoro(N-phenyl)methanesulfonamide (4) react with either reagent to yield mixtures of o- and p-fluoro-substituted derivatives.Solvent effects and competitive rate experiments demonstrate a preference for ortho substitution, especially in aprotic, nonpolar solvents.With particular substrates, these fluorinating agents are of practical synthetic utility, e.g., 2-fluoro-4-(trifluoromethyl)aniline is produced in high yield by fluorinating the intermediate 4-(trifluoromethyl)acetanilide (6) with CF3OF.Activated substrates such as toluene, xylenes, anisole, and cresols give mixtures of products which reduce the synthetic utility of these reagents.Nitrobenzene is fairly unreactive toward CF3OF and gives low yields of substitution products.
