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Salicylic Acid‐Catalyzed Arylation of Enol Acetates with Anilines
Author(s) -
FelipeBlanco Diego,
GonzalezGomez Jose C.
Publication year - 2018
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.201800427
Subject(s) - enol , chemistry , aryl , catalysis , silylation , salicylic acid , radical , organic chemistry , combinatorial chemistry , molecule , alkyl , biochemistry
α ‐Aryl ketones are both structure moieties commonly found in bioactive compounds and versatile synthetic intermediates for the preparation of drug‐like molecules. An operationally simple and scalable protocol has been developed to prepare α ‐aryl ketones from readily available aromatic amines and enol acetates (or silyl enol ethers). This metal‐free methodology features the use of salicylic acid as a convenient catalyst to promote the formation of aryl radicals from in‐situ generated aryl diazonium salts, without demanding thermal or photochemical activation. The mild reaction conditions used are compatible with anilines substituted with diverse functionalities. Structural elaboration of some prepared α ‐aryl ketones was accomplished to illustrate their usefulness as building blocks.