Overcoming the Challenges toward Selective C(6)-H Functionalization of 2-Pyridone with Maleimide through Mn(I)-Catalyst: Easy Access to All-Carbon Quaternary Center

An earth-abundant and inexpensive Mn(I)-catalyzed alkylation of 2-pyridone with maleimide has been reported for the first time, in contrast to previously reported Diels -Alder products. Notably, an unexpected rearrangement has been discovered in the presence of acetic acid, which also provides a unique class of compounds bearing three different N-heterocycles with an all-carbon quaternary center. Furthermore, single crystal X-ray and HRMS revealed a five-membered manganacycle intermediate. This methodology tolerates a wide variety of functional groups delivering the alkylated products in moderate to excellent yields.

Automated summary

An earth-abundant and inexpensive Mn(I)-catalyzed alkylation of 2-pyridone with maleimide has been reported for the first time, which demonstrates an unexpected rearrangement in the presence of acetic acid and provides a unique class of compounds. This methodology shows good tolerance towards various functional groups, delivering the alkylated products in moderate to excellent yields.