Direct Transformation of Alkylarenes into N‐(Pyridine‐2‐yl)amides by C(sp³)–C(sp³) Bond Cleavage

Abstract

C(sp3)–H bond functionalization and C(sp3)–C(sp3) bond cleavage are very challenging transformations in chemistry. Herein, we report a mild and green methodology for the construction of N‐(pyridine‐2‐yl)amides via tandem C(sp3)–H activation/C–C bond cleavage of alkylarenes. Various N‐heterocyclic amides were directly synthesized from alkylarenes in water in moderate to good yields.

Contemporary Approaches for Amide Bond Formation

“…Significantly, this marked the initial instance of synthesizing α-amino radicals from α-silyl amines without resorting to photochemical reaction conditions. Lastly, although reports exist of the direct αoxygenation of tertiary amines to secondary amides through CÀ N cleavage, [188] this reaction yields benzoic acid or benzaldehyde as by-products, consequently impacting the purification process.…”

“…Lastly, although reports exist of the direct α‐oxygenation of tertiary amines to secondary amides through C−N cleavage, [188] this reaction yields benzoic acid or benzaldehyde as by‐products, consequently impacting the purification process.…”