Metal-Free Intermolecular Coupling of Arenes with Secondary Amides: Chemoselective Synthesis of Aromatic Ketimines and Ketones, and N-Deacylation of Secondary Amides.
作者： Pei-Qiang Huang , Ying-Hong Huang , Kai-Jiong Xiao
关键词: Aldehyde 、 Nucleophile 、 Electrophile 、 Organic chemistry 、 Ketone 、 Nitrilium 、 Medicinal chemistry 、 Nitro 、 Amide 、 Chemistry 、 Chemoselectivity
摘要: The direct transformation of common secondary amides into aromatic ketimines and ketones with C–C bond formation is described. reaction can also be used for N-deacylation to release amines. This method consists in situ amide activation triflic anhydride intermolecular capture the resulting highly electrophilic nitrilium intermediate an arene. applicable various kinds (electrophiles), but only electron-rich moderately arenes as nucleophiles. Thanks use bench stable instead reactive basic organometallics nucleophiles, proceeded high chemoselectivity at amido group presence a series sensitive functional groups such aldehyde, ketone, ester, cyano, nitro, tertiary groups. viewed Friedel–Crafts-type using acylating agents or version o...
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