Bismuth-Mediated α-Arylation of Acidic Diketones with ortho-Substituted Boronic Acids.

ABSTRACT: The α-arylation of cyclic and fluoroalkyl 1,3-diketones is made challenging by the highly stabilized nature of the corresponding enolates, and is especially difficult for sterically demanding aryl partners. As a general solution to this problem, we report the Bi-mediated oxidative coupling of acidic diones and ortho-substituted arylboronic acids. Starting from a bench-stable bismacycle precursor, a sequence of B-to-Bi transmetallation, oxidation and C-C bond formation furnishes the arylated diones. Development of methodology that tolerates both sensitive functionality and steric demand is supported by interrogation of key reactive intermediates. Application of our strategy to cyclic diones enables the concise synthesis of important agrochemical intermediates which were previously prepared

SUBMITTER: Ruffell K 

PROVIDER: S-EPMC9805042 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature