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“Haliranium Ion”‐Induced Intermolecular Friedel‐Crafts Alkylation in HFIP: Synthesis of β,β‐Diaryl α‐Halo carbonyl Compounds
Author(s) -
Bhattacharya Aditya,
mani Shukla Pushpendra,
Maji Biswajit
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100823
Subject(s) - friedel–crafts reaction , chemistry , intermolecular force , alkylation , computational chemistry , halo , ion , organic chemistry , photochemistry , combinatorial chemistry , catalysis , molecule , physics , quantum mechanics , galaxy
Here reports a highly regio‐ and diastereoselective haliranium ion‐induced intermolecular Friedel‐Crafts reaction of α,β‐unsaturated carbonyl compounds in HFIP. The operationally simple and mild method affords the synthetically useful β,β‐diarylated α‐halo carbonyl compounds in good yields after a very short reaction time. As an application, a few examples of β,β‐diarylated olefins are prepared in excellent yields. Based on the experimental results and a qualitative study of 1D‐NMR‐experiments, a plausible reaction mechanism is proposed.