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Multicomponent Cascade Synthesis of Biaryl‐Based Chalcones in Pure Water and in an Aqueous Micellar Environment
Author(s) -
Armenise Nicola,
Malferrari Danilo,
Ricciardulli Sara,
Galletti Paola,
Tagliavini Emilio
Publication year - 2016
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.201600095
Subject(s) - chemistry , reagent , catalysis , aqueous solution , combinatorial chemistry , cascade , organic chemistry , aryl , aqueous medium , aldol condensation , cascade reaction , alkyl , chromatography
The challenging multicomponent cascade synthesis of biaryl‐based chalcones was carried out in pure water and in an aqueous micellar system. The first step of the protocol was a simple Pd‐catalysed, ligand‐free, and aerobic Suzuki–Miyaura reaction in aqueous medium. This proved to be extremely efficient for the coupling of aryl and heteroaryl bromides with different arylboronic acids. Subsequently, the resulting intermediates underwent an in‐situ aldol condensation reaction to give biaryl(hetero)chalcones in good to excellent yields. When the protocol was applied to highly lipophilic or less reactive reagents, micellar catalysis was required for good results. To achieve this, we successfully used a new surfactant obtained from renewable resources that we recently designed. Furthermore, using this additive, the catalytic system can be repeatedly recycled without significant loss of activity.