A S-O bond insertion reaction of sulfoxides with arynes is reported. This reaction represents a rare instance of semipolar single bond insertion in aryne chemistry. The study of mechanism indicates that a sulfur ylide triggered by aryne is the key intermediate, which further transfers its methylene group to carbonyl compounds to give epoxides and thioethers through a sequential process.
An efficient method for the synthesis of epoxides from carbonyl compounds, sulfoxides, and benzyne is presented. The strategy involved an epoxidation by a sulfur ylide which is formed in situ from sulfoxide and benzyne through the S-O bond insertion and deprotonation. This one-pot reaction proceeds under mild and base-free conditions, providing a convenient way to introduce the substituted methylene groups onto the carbonyl carbon.
Am ild ande fficientc ascade synthesis of 1,5-diketones from readily available N,N-dicyclohexylmethylamine,1 ,3-dicarbonyl compounds,a nd trifluoromethyl b-diketones hasb een developed. This cascade reactiono ccurs via an oxidation/Mannich reaction/Cope elimination/Michael addition/ retro-Claisen reactions equence,a nd provides multiple C À Cb ond formations in one pot. In addition, exquisite chemoselectivity is achieved in the reaction between 1,3-dicarbonyl compounds and trifluoromethyl b-diketones.
1,5-Diketones Synthesis via Three-Component Cascade Reaction. -The new cascade synthesis of 1,5-diketones from readily available N,N-dicyclohexylmethylamine (III), 1,3-dicarbonyl compounds, and trifluoromethyl -diketones occurs via an oxidation/Mannich reaction/Cope elimination/Michael addition/retro-Claisen reaction sequence, and provides multiple C-C bond formations in one pot. In addition, excellent chemoselectivity is achieved in that reaction. -(XING, L.-J.; LU, T.; FU, W.-L.; LOU, M.-M.; CHEN, B.; WANG, Z.-S.; JIN, Y.; LI, D.; WANG*, B.; Adv. Synth. Catal. 357 (2015) 14-15, 3076-3080, http://dx.
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