Remote Nucleophilic Substitution at a C(sp)-H Bond of α-Bromocarboxamides via 1,4-Hydrogen Atom Transfer To Access -Acyl-,-acetal Compounds.

Herein, we report a remote nucleophilic substitution reaction via 1,4-hydrogen atom transfer (1,4-HAT) to synthesize -acyl-,-acetal moieties. α-Bromocarboxamide undergoes rS at a C(sp)-H bond in the presence of an alcohol/phenol and a copper catalyst. Mechanistic studies using deuterated α-bromocarboxamide confirmed that the 1,4-HAT process is the rate-determining step. Topologically complex -acyl-,-acetal molecules can be accessed using our rS reaction with various α-bromocarboxamides via chemoselective reactions.