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Ligand‐Free Suzuki Cross‐Coupling Reactions: Application to β‐Halo‐α,β‐Unsaturated Aldehydes
Author(s) -
Gogoi Pranjal,
Bezboruah Pranjal,
Boruah Romesh C.
Publication year - 2013
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.201300491
Subject(s) - chemistry , suzuki reaction , ligand (biochemistry) , aryl , boronic acid , aldol condensation , organic chemistry , combinatorial chemistry , aqueous medium , condensation , cascade , coupling reaction , aqueous solution , catalysis , alkyl , biochemistry , receptor , physics , thermodynamics , chromatography
A facile, efficient, ligand‐free Suzuki–Miyaura reaction of β‐halo α,β‐unsaturated aldehydes with boronic acids in aqueous media at room temperature is described. Under the optimized conditions, both steroidal and nonsteroidal β‐halo α,β‐unsaturated aldehydes reacted rapidly with the boronic acids to provide a series of aryl‐substituted derivatives in excellent yields. Moreover, the protocol was extended to the direct one‐pot synthesis of polycyclic aromatic hydrocarbons through a Suzuki–Miyaura cross‐coupling/aldol condensation cascade reaction under microwave irradiation.