Catalyst-Free Suzuki-Type Coupling of Allylic Bromides with Arylboronic Acids

The coupling of arylboronic acids with electron‐rich allylic bromides is accomplished in the absence of any transition‐metal catalyst through conventional heating. The reaction is completely regioselective, affording only the α‐coupled product, and can be carried out under mild aerobic conditions in...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2012-01, Vol.2012 (2), p.264-268
Main Authors: Scrivanti, Alberto, Beghetto, Valentina, Bertoldini, Matteo, Matteoli, Ugo
Format: Article
Language:English
Subjects:
Allylation
B derivatives
Boron
C-C coupling
Catalysis
Catalysts: preparations and properties
Chemistry
Cross-coupling
Exact sciences and technology
General and physical chemistry
Noncondensed benzenic compounds
Organic chemistry
Organometalloidal and organometallic compounds
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:The coupling of arylboronic acids with electron‐rich allylic bromides is accomplished in the absence of any transition‐metal catalyst through conventional heating. The reaction is completely regioselective, affording only the α‐coupled product, and can be carried out under mild aerobic conditions in an organic solvent; the presence of a base is required. A catalyst‐free protocol for the synthesis of allylated arenes has been developed. Allylic bromides bearing electron‐donating groups can be regioselectively coupled with arylboronic acids in fair to good yields without the need for a transition‐metal catalyst. The coupling is easily accomplished through conventional heating under aerobic conditions in the presence of an inorganic base.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201101527