Copper(i)-catalyzed radical carboamination reaction of 8-aminoquinoline-oriented buteneamides with chloroform: synthesis of-β-lactams.

A novel Cu(CHCN)PF-catalyzed carboamination reaction of 8-aminoquinoline-oriented buteneamides with chloroform to afford 4-(2,2,2-trichloroethyl)-β-lactams is described. The reaction proceeded at 110 °C in air with di--butyl peroxide. Preliminary studies indicated that the reaction undergoes a free radical mechanism a Cu(i)/Cu(ii)/Cu(iii) catalytic cycle.

A practical copper-catalyzed approach to β-lactams via radical carboamination of alkenyl carbonyl compounds.

Functionalized β-lactams are highly important motifs in synthetic chemistry. We report an efficient and novel approach to the synthesis of β-lactams via a copper(i)-catalyzed cascade process involving C(benzyl)-H radical abstraction, intermolecular alkene addition, and intramolecular amination reaction. Variously substituted alkenes were synthesized from vinylacetic acid, leading to the corresponding β-lactams in moderate to good yields.