Transition‐Metal‐Free DMAP‐Mediated Aromatic Esterification of Amides with Organoboronic Acids

Abstract

A new, transition‐metal‐free, effective method for aromatic esterification of amides with organoboronic acids has been developed. A wide range of benzoate derivatives were obtained with yields ranging from moderate to good. The catalytic reaction shows a broad substrate scope and excellent functional group tolerance. Conceptually, DMAP mediates the reaction and is crucial for this transformation.

DABCO-catalyzed esterification of N-pivaloyl-activated amides

“…In an alternate approach, aryl boronic acids were used instead of phenolic substrates. The reaction was mediated by DMAP–TBHP 30 in one of the approaches and by K 3 PO 4 -visible light in another method. 31 On the other hand, Hua-Li Qin et al 32 developed a complementary strategy where alcohol substrates were activated by SO 2 F 2 to function as electrophiles rather than as nucleophiles in the esterification of amides.…”