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Hypervalent Iodine‐Promoted Aromatization of Exocyclic β‐Enaminones for the Synthesis of meta ‐ N , N ‐Diarylaminophenols
Author(s) -
Bhattacherjee Dhananjay,
Thakur Vandna,
Shil Arun K.,
Das Pralay
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700004
Subject(s) - hypervalent molecule , chemistry , aromatization , tandem , halogenation , iodine , stereochemistry , cyclohexenone , combinatorial chemistry , organic chemistry , catalysis , materials science , composite material
A metal‐ and additive‐free milder cascade approach for the synthesis of meta ‐ N , N ‐diarylaminophenols (DAAP) starting from exocyclic β‐enaminones has been developed. The feasibility of the process is rationalized by the suitable molecular geometry of β‐enaminones for tandem N ‐arylative α‐iodination and aromatization under milder basic conditions. Furthermore, the developed strategy has been extended to the synthesis of meta ‐ N ‐benzyl‐ N ‐arylaminophenols (BAAP). 4‐Ethylpropionyl‐2‐cyclohexenone has been explored to give 7‐diarylaminochroman‐2‐one (DAAC) by employing a similar one‐pot approach. The plausible mechanistic steps were deduced based upon isolation of a stable intermediate and structural identification through X‐ray crystallographic analysis.