Suzuki–Miyaura Coupling Reactions of Iodo(difluoroenol) Derivatives, Fluorinated Building Blocks Accessible at Near-Ambient Temperatures

Abstract

A recently developed method for the near-ambient generation of difluorovinylzinc reagents has facilitated the preparation of 1-(<i>N</i>,<i>N</i>-diethylcarbamoyloxy)-2,2-difluoro-1-iodoethene and 2,2-difluoro-1-iodo-1-(2′-methoxyethoxymethoxy)­ethene. The utility of these reagents has been investigated in Suzuki–Miyaura couplings with a range of potassium trifluoroborate coupling partners, with the scope of successful couplings proving wide. Deiodinated species appeared as significant side products, but a solvent change from <i>i</i>-PrOH to <i>t</i>-BuOH suppressed the pathway to these species and improved coupling yields