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A Highly Regioselective and Practical Synthesis of α‐Aryl Ketones under a Cooperative Cascade Effect of an Ionic Liquid and Tetrabutylammonium Fluoride
Author(s) -
Thopate Yogesh,
Singh Richa,
Rastogi Sumit K.,
Sinha Arun K.
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.201900513
Subject(s) - regioselectivity , chemistry , ketone , aryl , ionic liquid , epoxide , tetralone , organic chemistry , tetrabutylammonium fluoride , diol , catalysis , combinatorial chemistry , alkyl
A metal‐free regioselective synthesis of α‐aryl ketone from corresponding bromohydrin via cooperative cascade effect of [hmim]Br and tetrabutylammonium fluoride under microwave irradiation is reported. Applications of the protocol are illustrated by synthesis of drug intermediates piperonyl‐methyl ketone and 2‐tetralone. Interestingly, direct regioselective transformation of epoxide and 1,2‐diol into α‐aryl ketone under neat [hmim]Br has also been realized. Advantages of this method are demonstrated through the recyclability of [hmim]Br‐tetrabutylammonium fluoride catalytic system and gram scalability.