83375-43-3Relevant academic research and scientific papers
Stereospecific Electrophilic Fluorocyclization of α,β-Unsaturated Amides with Selectfluor
Fei, Haiyang,Fu, Yao,Jalani, Hitesh B.,Li, Guigen,Lu, Hongjian,Wu, Hongmiao,Xu, Zheyuan,Zhu, Lin
, (2020/03/30)
An efficient fluorocyclization of α,β-unsaturated amides through a formal halocyclization process is developed. The reaction proceeds under transition-metal-free conditions and leads to the formation of fluorinated oxazolidine-2,4-diones with excellent regio- and diastereoselectivity. The evaluation of the reaction mechanism based on preliminary experiments and density functional theory calculations suggests that a synergetic syn-oxo-fluorination occurs and is followed by an anti-oxo substitution reaction. The reaction opens a new window in the field of stereospecific fluorofunctionalization.
All-carbon-substituted quaternary carbon atoms in oxindoles by an aerobic palladium(II)-catalyzed ring closure onto tri- and tetrasubstituted double bonds
Schiffner, Julia A.,Oestreich, Martin
supporting information; experimental part, p. 1148 - 1154 (2011/04/15)
Oxidative palladium(II)-catalyzed cyclization of α,β-unsaturated amides derived from electron-rich anilines is reported. The aerobic ring closure of tri- and tetrasubstituted alkenes yields oxindoles with congested all-carbon-substituted quaternary carbon atoms. The ring-size selectivity is excellent. Selected unsymmetrically substituted arenes cyclize with perfect regioselectivity. Experimental evidence indicates that the mechanism is likely to involve Friedel-Crafts-type electrophilic substitution rather than direct C-H bond activation. Oxindoles are formed in an aerobic palladium(II)-catalyzed cyclization of tri- and tetrasubstituted double bonds at relatively low catalyst loading. The mechanism likelyinvolves a Friedel-Crafts-type electrophilic substitution rather than direct C-H bond activation.
