Visible light-mediated transition metal-free esterification of amides with boronic acids

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

“…Besides these advances, Zeng and co‐workers [11] showed a new protocol for the aerobic oxidative coupling of amides with arylboronic acids using the fluoride and palladium as cooperative catalysis (Scheme 1B). Despite the impressive progress made so far in the transformations, the optimization and development of new conceptual methods to convert amides to esters are still an attractive research topic [12] . In our previous work, we have developed efficient catalytic systems for the Suzuki‐Miyaura cross‐coupling of N‐acylsuccin imides with arylboronic acids via C−N bond activation [13] .…”

“…Despite the impressive progress made so far in the transformations, the optimization and development of new conceptual methods to convert amides to esters are still an attractive research topic. [12] In our previous work, we have developed efficient catalytic systems for the Suzuki-Miyaura cross-coupling of N-acylsuccin imides with arylboronic acids via CÀ N bond activation. [13] These leading results encourage us to develop new synthetic methods based on CÀ N bond cleavage of amides under exceedingly mild conditions.…”

DABCO-catalyzed esterification of N-pivaloyl-activated amides

“…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. Notably, all the above protocols relied on amides that are twisted, resonance destabilized, and/or tertiary amides.…”