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We describe the development of an intermolecular unactivated C(sp 3 )-H bond functionalization towards the direct synthesis of tertiary carbamates. The transformation proceeded using a readily available, abundant first-row transition metal catalyst (copper), and isocyanates as the source of the amide moiety. This is a novel strategy for direct transformation of a variety of unactivated hydrocarbon feedstocks to N -alkyl- N -aryl and N , N -dialkyl carbamates without pre-functionalization or installation of a directing group. The reaction had a broad substrate scope with 3° &gt; 2° &gt; 1° site selectivity. The reaction proceeded even on a gram scale, and a corresponding free amine was directly obtained when the reaction was performed at high temperature. Kinetic studies suggested that radical-mediated C(sp 3 )-H bond cleavage was the rate-determining step.

Copper-catalyzed intermolecular C(sp3)–H bond functionalization towards the synthesis of tertiary carbamates

Copper-catalyzed intermolecular C(sp³)–H bond functionalization towards the synthesis of tertiary carbamates