Electrochemically Enabled Chan-Lam Couplings of Aryl Boronic Acids and Anilines.

The Chan-Lam reaction remains a highly utilized transformation for C-N bond formation. However, anilines remain problematic substrates due to their lower nucleophilicity. To address this problem, we developed an electrochemically mediated Chan-Lam coupling of aryl boronic acids and amines utilizing a dual copper anode/cathode system. The mild conditions identified have enabled the preparation of a wide range of functionalized biarylanilines in good yields and chemoselectivities.

Stereoselective Synthesis of Trisubstituted Alkenylboron Reagents by Boron-Wittig Reaction of Ketones.

Application of the boron-Wittig reaction to ketone electrophiles provides a straightforward route to trisubstituted alkenylboronic esters. With either a pentamethyldiethylenetriamine or trimethyl-1,4,7-triazacyclononane additive, the olefination can occur with very high levels of stereocontrol and in good chemical yield.