17559-70-5Relevant academic research and scientific papers
C?H Alkenylation of Pyrroles by Electronically Matching Ligand Control
Kim, Hyun Tae,Lee, Woohyeong,Kim, Eunmin,Joo, Jung Min
, p. 2418 - 2422 (2018)
Directing group and substrate control strategies have frequently been employed for the regioselective C?H alkenylation of acid- and oxidant-sensitive pyrrole heterocycles. We developed an undirected, aerobic strategy for the C?H alkenylation of N-alkylpyrroles by ligand control. For C2-alkenylation of electron-rich N-alkylpyrroles, an electrophilic palladium catalyst derived from Pd(OAc)2 and 4,5-diazafluoren-9-one (DAF) was used. Alternatively, a combination of Pd(OAc)2 and a mono-protected amino acid ligand, Ac-Val-OH, was useful for C5-alkenylation of N-alkylpyrroles possessing electron-withdrawing groups at the C2 position. This approach based on the electronic effects of heterocycles and catalysts can rapidly provide a wide range of alkenyl pyrroles from readily available N-alkylpyrroles and alkenes.
