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Synfacts 2014; 10(1): 0072
DOI: 10.1055/s-0033-1340365
DOI: 10.1055/s-0033-1340365
Metal-Mediated Synthesis
Palladium-Catalyzed Anti-Markovnikov Hydroalkylation of Homoallylic Alcohols
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
13. Dezember 2013 (online)
Significance
Lin and Qing report a mild and convenient protocol for the anti-Markovnikov hydroalkylation of β,β-difluorinated homoallylic alcohols. The palladium-catalyzed reaction with alkylzinc reagents furnishes the products in good to excellent yields.
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Comment
The reported protocol affords a wide range of synthetically useful gem-difluorinated compounds with good functional-group compatibility. Moreover, the results show that the transposition of CH2 into CF2 at the allylic position of homoallylic alcohols can modify the electronic and steric environment of the alkene.
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