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Heteroaromatic Aldehydes with Unprecedented Catalytic Performance in Selective Radical Reactions: Synthesis of α‐Aminophosphonate Scaffolds
Author(s) -
Aghahosseini Hamideh,
Ramazani Ali,
Taran Jafar,
Ślepokura Katarzyna,
Lis Tadeusz
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900241
Subject(s) - chemistry , catalysis , radical , combinatorial chemistry , alkyl , organic synthesis , organic chemistry , peptidomimetic , solvent , peptide , biochemistry
Heterocyclic compounds have gained immense importance because of their low resonance energy and strong hydrogen‐bonding abilities, which provide good catalytic potential in a variety of organic transformations. Herein an unexpected metal‐free catalytic performance of heteroaromatic aldehydes has been reported. Accordingly, a unique method for the synthesis of new scaffolds of peptidomimetic compounds, α‐aminophosphonates has been developed, which was difficult using previous methods. The aerobic auto‐oxidation of heteroaromatic aldehydes acts as a driving force for the coupling of aromatic N ‐benzylamines and hydrophosphoryl compounds according to a one‐pot, metal‐ and solvent‐free procedure. Heteroaromatic aldehydes, in addition to their individual ability to promote selective radical reactions through the auto‐oxidation process, can provide hydrogen bonding frameworks at different stages of the reaction and thereby change the reaction pathways and induce new activities and selectivities, which unveiled their other important catalytic features. We believe that this highlights the catalytic potential of heteroaromatic aldehydes, which may offer an opportunity to change the traditional harsh conditions necessary to generate alkyl radicals.