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α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation
Author(s) -
Zawodny Wojciech,
Teskey Christopher J.,
Mishevska Magdalena,
Völkl Martin,
Maryasin Boris,
González Leticia,
Maulide Nuno
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202006398
Subject(s) - electrophile , nucleophile , ketone , chemistry , ring (chemistry) , combinatorial chemistry , metal , triflic acid , organic chemistry , catalysis
Triflic anhydride mediated activation of acetophenones leads to highly electrophilic intermediates that can undergo a variety of transformations when treated with nucleophiles. This electrophilic ketone activation gives access to α‐arylated and α‐oxyaminated acetophenones under metal‐free conditions in moderate to excellent yields and enables extension to the synthesis of arylated morpholines via generation of vinylsulfonium salts. Computational investigations confirmed the transient existence of intermediates derived from vinyl triflates and the role of the oxygen atoms at the para position of aromatic ring in facilitating their stabilisation.