Mechanistic Insights into Direct Amide Bond Formation Catalyzed by Boronic Acids: Halogens as Lewis Bases

Get the water out! DFT calculations predict water elimination from a tetrahedral intermediate to be the rate determining step in the title reaction. This transformation is calculated to be highly stereoselective, yielding cis amides as the kinetic products (see scheme). The superior activity of ortho-halophenyl boronic acids results from the Lewis basic character of halogen atoms. Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.