Ligand-Free Suzuki Cross-Coupling Reactions: Application to [beta]-Halo-[alpha],[beta]-Unsaturated Aldehydes

A facile, efficient, ligand-free Suzuki-Miyaura reaction of [beta]-halo [alpha],[beta]-unsaturated aldehydes with boronic acids in aqueous media at room temperature is described. Under the optimized conditions, both steroidal and nonsteroidal [beta]-halo [alpha],[beta]-unsaturated aldehydes reacted...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-08, Vol.2013 (23), p.5032
Main Authors: Gogoi, Pranjal, Bezboruah, Pranjal, Boruah, Romesh C
Format: Article
Language:English
Subjects:
Beta
Ligands
Polycyclic aromatic hydrocarbons
Online Access:Get full text
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Summary:A facile, efficient, ligand-free Suzuki-Miyaura reaction of [beta]-halo [alpha],[beta]-unsaturated aldehydes with boronic acids in aqueous media at room temperature is described. Under the optimized conditions, both steroidal and nonsteroidal [beta]-halo [alpha],[beta]-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. [PUBLICATION ABSTRACT]
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300491