Palladium-Catalyzed and Hybrid Acids-Assisted Synthesis of [60]Fulleroazepines in One Pot under Mild Conditions: Annulation of N-Sulfonyl-2-aminobiaryls with [60]Fullerene through Sequential C-H Bond Activation, C-C and C-N Bond Formation
The palladium-catalyzed one-pot synthesis of 2,3-deoxy-3-keto aryl C-glycosides is achieved from glycals and anilines in the presence of tert-butyl nitrite and aqueous HBF4 under mild conditions. This one-pot method stereospecifically provides α- and β-aryl glycosides (≥19:1 by NMR) in good yields at room temperature. The configuration at the C-3 position in the glycal determines the anomeric selectivity (i.e., α or β) of the desired products.
A K2CO3-catalyzed one-pot protocol involving sequential C–C bond formation and cleavage of aromatic β-diketones with α,β-unsaturated esters is developed to obtain 1,5-ketoesters, proceeding smoothly under mild conditions in up to 98% isolated yield.
The first example of carbon double-bond formation via praseodymium-mediated Barbier type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported. The reaction is highly α-regioselective and conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with practical reaction conditions.
The carbon–carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly α-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with feasible reaction conditions.
A copper-catalyzed direct sulfoxidation reaction by C(sp3)–H bond activation has been developed. Starting from sample aromatic methyl thioethers with aryl halides, versatile biologically-active arylbenzylsulfoxide derivatives were efficiently synthesized in good to high yields under mild conditions. This new methodology provides an economical approach toward C(sp3)–C(sp2) bond formation.
An Electron-Poor C64
Nanographene by Palladium-Catalyzed Cascade C−C Bond Formation: One-Pot Synthesis and Single-Crystal Structure Analysis