Regioselective ortho halogenation of N-aryl amides and ureas via oxidative halodeboronation: harnessing boron reactivity for efficient C-halogen bond installation.

ABSTRACT: The installation of the C-halogen bond at the ortho position of N-aryl amides and ureas represents a tool to prepare motifs that are ubiquitous in biologically active compounds. To construct such prevalent bonds, most methods require the use of precious metals and a multistep process. Here we report a novel protocol for the long-standing challenge of regioselective ortho halogenation of N-aryl amides and ureas using an oxidative halodeboronation. By harnessing the reactivity of boron over nitrogen, we merge carbonyl-directed borylation with consecutive halodeboronation, enabling the precise introduction of the C-X bond at the desired ortho position of N-aryl amides and ureas. This method offers an efficient, practical, and scalable solution for syn

SUBMITTER: Shinde GH 

PROVIDER: S-EPMC10685333 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature