Cooperative Cu/azodiformate system-catalyzed allylic C-H amination of unactivated internal alkenes directed by aminoquinoline.

ABSTRACT: Aliphatic allylic amines are common in natural products and pharmaceuticals. The oxidative intermolecular amination of C(sp³)-H bonds represents one of the most straightforward strategies to construct these motifs. However, the utilization of widely internal alkenes with amines in this transformation remains a synthetic challenge due to the inefficient coordination of metals to internal alkenes and excessive coordination with aliphatic and aromatic amines, resulting in decreasing the reactivity of the catalyst. Here, we present a regioselective Cu-catalyzed oxidative allylic C(sp³)-H amination of internal olefins with azodiformates to these problems. A removable bidentate directing group is used to control the regiochemistry and stabilize the π-allyl-metal intermediat

SUBMITTER: Wang L 

PROVIDER: S-EPMC10876528 | biostudies-literature | 2024 Feb

REPOSITORIES: biostudies-literature