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Synfacts 2014; 10(1): 0072
DOI: 10.1055/s-0033-1340365
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Anti-Markovnikov Hydroalkylation of Homoallylic Alcohols

Contributor(s):
Paul Knochel
,
Christoph Sämann
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
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Publication History

Publication Date:
13 December 2013 (online)

 
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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.


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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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