The Copper Mediated Barbier Reactions of α,β-Unsaturated Ketones: Regioselective Conjugate and 1,2-Addition

Costello, Declan P.; Geraghty, Niall W. A.

doi:10.1080/00397919908085932

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1999

2010

Publication Types

Select...

Article2

Other1

Book1

Relationship

Self Cite0

Independent4

Authors

Journals

Cited by 4 publications

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Barbier Reaction

2010

Comprehensive Organic Name Reactions and Reagents

View full text Add to dashboard Cite

In the Barbier reaction, both alkyl halides and carbonyl compounds are simultaneously mixed with magnesium turnings and form carbon‐carbon bonds in one‐step. It has been reported that small excess of the toxic halide can be used, and similar results, including the R:S ratio, with respect to the Grignard reaction can be obtained. This reaction is known to be preferable for halides and is believed to go through the single‐electron transfer (SET) process. Presently, many zero‐valent metals have been successfully applied to similar reaction conditions. It has been reported that nonpolar solvents favor R‐regioselection whereas polar solvents lead to γ‐ syn selection. This reaction has wide applications in organic synthesis.

show abstract

Barbier Reaction

2010

Comprehensive Organic Name Reactions and Reagents

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: The Copper Mediated Barbier Reactions of α,β‐Unsaturated Ketones: Regioselective Conjugate and 1,2‐Addition.

Costello

Geraghty

1999

ChemInform

View full text Add to dashboard Cite

The Copper Mediated Barbier Reactions of α,β-Unsaturated Ketones: Regioselective Conjugate and 1,2-Addition.-The one-pot reaction of isophorone (I) and other α,β-unsaturated ketones such as (V) and (VII) with alkyl and aryl halides (II) in the presence of magnesium and copper salts (Barbier conditions) leads to the regiospecific formation of 1,4-addition products. Contrary, Li-mediated reaction of model compound (I) with halides (II) results in regioselective 1,2-addition [→(IV)]. -(COSTELLO, DECLAN P.; GERAGHTY, NIALL W. A.; Synth. Commun. 29 (1999) 18, 3083-3096; Chem. Dep., Nat. Univ. Ire., Galway, Ire.; EN)

show abstract

Alkynes

Tyrrell

2005

Comprehensive Organic Functional Group Transformations II

View full text Add to dashboard Cite

The Copper Mediated Barbier Reactions of α,β-Unsaturated Ketones: Regioselective Conjugate and 1,2-Addition

Cited by 4 publications

References 19 publications

Barbier Reaction

Barbier Reaction

ChemInform Abstract: The Copper Mediated Barbier Reactions of α,β‐Unsaturated Ketones: Regioselective Conjugate and 1,2‐Addition.

Alkynes

Contact Info

Product

Resources

About