jo500139z_si_001.pdf (6.79 MB)
Preparation of Tetrasubstituted 3‑Phosphonopyrroles through Hydroamination: Scope and Limitations
journal contribution
posted on 2014-05-16, 00:00 authored by Wouter Debrouwer, Thomas
S. A. Heugebaert, Christian V. StevensPhosphonylated
pyrroles were obtained by a ZnCl2-catalyzed
5-exo-dig hydroamination of propargylic
enamines. These starting compounds were obtained in two steps from
commercially available β-ketophosphonates. The method tolerates
a wide variety of substituents at the 1,2- and 5-position of the pyrrole,
while further derivatization allows for the introduction of substituents
at the 4-position via lithiation or halogenation.