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Friedel–Crafts Arylation of α‐Hydroxy Ketones: Synthesis of 1,2,2,2‐Tetraarylethanones
Author(s) -
Kumar Anil,
Singh Tej V.,
Thomas Sajesh P.,
Venugopalan Paloth
Publication year - 2015
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.201403438
Subject(s) - chemistry , friedel–crafts reaction , triflic acid , steric effects , lewis acids and bases , stoichiometry , brønsted–lowry acid–base theory , carbocation , organic chemistry , medicinal chemistry , catalysis
Friedel–Crafts arylation of α‐hydroxy ketones such as 2‐hydroxy‐1,2,2‐triarylethanones has been achieved with a variety of arenes and heteroarenes in the presence of Lewis or Brønsted acids. Both sterically hindered and unhindered 1,2,2,2‐tetrarylethanones are formed in good to excellent yields by using a stoichiometric amount of triflic acid. The intermediacy of an α‐keto carbenium ion has been proposed.