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Heteroaromatic aldehydes with unprecedented catalytic performance in selective radical reactions : synthesis of α‐aminophosphonate scaffolds
Autorzy
Rok wydania
2019
Czasopismo
Asian Journal of Organic Chemistry
Numer woluminu
8
Strony
1519-1527
DOI
10.1002/ajoc.201900241
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
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.
Słowa kluczowe
Aldehydes, aerobic auto-oxidation, aminophosphonates, heterocycles, radical reactions
Adres publiczny
http://dx.doi.org/10.1002/ajoc.201900241
Strona internetowa wydawcy
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