Lin X, Qing F.-L * Shanghai Institute of Organic Chemistry and Donghua University,
Shanghai, P. R. of China
Palladium-Catalyzed Anti-Markovnikov Hydroalkylation of Homoallylic Alcohols Bearing
β-Fluorines.
Org. Lett. 2013;
15: 4478-4481
Key words
anti-Markovnikov hydroalkylation - homoallylic alcohols - zinc
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.
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.
