Radical aminoalkylation of maleimides with alkylamines and alkanes

• Published in: Applied organometallic chemistry Vol. 37; no. 2
• Main Authors: Li, Jia, Zhang, Wenliang, Li, Yu‐An, Wu, Ge, Zhang, Xu
• Format: Journal Article
• Language: English
• Published: HOBOKEN Wiley 01.02.2023; Wiley Subscription Services, Inc
• Subjects: Alkanes; Alkylamines; Alkylation; Amines; carboamination; Chemistry; Chemistry, Applied; Chemistry, Inorganic & Nuclear; copper catalysis; maleimides; Physical Sciences; relay catalysis; Science & Technology; three‐component reactions; three-component reactions; copper catalysis; ALKENES; AEROBIC OXIDATIVE AMINATION; AMINES; ALKYLATION; relay catalysis; carboamination; 3-COMPONENT CARBOAMINATION; maleimides; ENAMIDES
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.6974

A meaningful copper‐catalyzed chemo‐selective oxidative alkylamination of maleimides with secondary alkyl amines and simple alkanes has been developed. This transformation exhibits excellent compatibility with an array of polyfunctionalized organic amines and inactivated alkanes, modular synthesis of 3‐carbo‐4‐amino maleimides under simple, and efficient catalytic systems. Detailed mechanistic studies support the formation of 3‐amino maleimides and alkyl radical intermediates and their subsequent radical alkylation in the reaction process. A meaningful copper‐catalyzed chemo‐selective oxidative alkylamination of maleimides with secondary alkyl amines and simple alkanes has been developed. This transformation exhibits excellent compatibility with an array of polyfunctionalized organic amines and inactivated alkanes, modular synthesis of 3‐carbo‐4‐amino maleimides under simple, and efficient catalytic systems. Detailed mechanistic studies support the formation of 3‐amino maleimides and alkyl radical intermediates and their subsequent radical alkylation in the reaction process.