Palladium-catalyzed highly diastereoselective cascade dihalogenation of alkyne-tethered cyclohexadienones via Umpolung of palladium enolate

Herein, we report a highly diastereo- and regioselective dihalogenation of alkyne-tethered cyclohexadienones for the synthesis of cis -hydrobenzofurans. One carbon–carbon and two carbon–halogen bonds were formed in an efficient manner and three contiguous stereocenters were generated. The reaction p...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019, Vol.55 (89), p.13442-13445
Main Authors: Singh, Anurag, Shukla, Rahul K., Volla, Chandra M. R.
Format: Article
Language:English
Subjects:
Alkynes
Carbon
Crystallography
Palladium
Stereoselectivity
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Summary:Herein, we report a highly diastereo- and regioselective dihalogenation of alkyne-tethered cyclohexadienones for the synthesis of cis -hydrobenzofurans. One carbon–carbon and two carbon–halogen bonds were formed in an efficient manner and three contiguous stereocenters were generated. The reaction proceeds through cis -halopalladation, migratory insertion followed by a nucleophilic attack of a halide anion on a palladium enolate.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc07164d