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