Development of copper-catalyzed deaminative esterification using high-throughput experimentation.

ABSTRACT: Repurposing of amine and carboxylic acid building blocks provides an enormous opportunity to expand the accessible chemical space, because amine and acid feedstocks are typically low cost and available in high diversity. Herein, we report a copper-catalyzed deaminative esterification based on C-N activation of aryl amines via diazonium salt formation. The reaction was specifically designed to complement the popular amide coupling reaction. A chemoinformatic analysis of commercial building blocks demonstrates that by utilizing aryl amines, our method nearly doubles the available esterification chemical space compared to classic Fischer esterification with phenols. High-throughput experimentation in microliter reaction droplets was used to develop the reaction, along with classic scope studi

SUBMITTER: Shen Y 

PROVIDER: S-EPMC9814592 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature