posted on 2023-12-18, 21:03authored byHaozhi Wu, Kang Chen, Yunyun Liu, Jie-Ping Wan
The C–N bond transamidation
of primary amides with N,N-dimethyl
enaminones has been efficiently
realized by heating in the presence of trifluoromethanesulfonic acid
(TfOH). The method enables the practical synthesis of valuable enamides
without the use of any metal reagent. In addition, this transamidation
protocol can also be expanded to the reactions of sulfonamides, and
the late-stage functionalization on sulfonamide drugs such as Celecoxib
and Valdecoxib has been verified. Moreover, the participation of water
in assisting the transamidation process has been identified by the
isotope labeling experiments using D2O, disclosing a new
possibility in designing catalytic tactic to other transamidation
reactions.