jo9b02733_si_001.cif (454.27 kB)
Iron-Catalyzed Transfer Hydrogenation in Aged N‑Methyl-2-pyrrolidone: Reductive Ring-Opening of 3,5-Disubstituted Isoxazoles and Isoxazolines
dataset
posted on 2019-12-11, 13:12 authored by Xiaochen Liu, Dongsub Hong, Netanel G. Sapir, Wen Yang, William H. Hersh, Pak-Hing Leung, Dingqiao Yang, Yu Chen3,5-Disubstituted isoxazoles and isoxazolines undergo
an iron-catalyzed
reductive ring-opening in aged N-methyl-2-pyrrolidone
(NMP). 5-Hydroxy-N-methyl-2-pyrrolidone generated in situ via a simple activation of commercial NMP acts as
the hydrogen donor in the iron-catalyzed transfer hydrogenation reaction.
It is the first example employing a combination of an iron catalyst
and 5-hydroxy-N-methyl-2-pyrrolidone as reducing
agents in a transfer hydrogenation reaction. The protocol is highly
efficient for the synthesis of β-enaminones and 1,3-diketones,
providing a versatile route for the preparation of these 1,3-difunctional
compounds bearing diversified substitution patterns.