Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 28, Pages 8516-8521Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000227
Keywords
alkynes; C-C bond formation; ketones; superbases; vinylation
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Funding
- Russian Foundation of Basic Research [08-03-00002]
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Alkylaryl- and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100 degrees C, 1 h) to give regio- and stereoselectively the (E)-beta-gamma-ethylenic ketones ((E)-3-buten-1-ones) in 61-84% yields and with approximately 100% stereoselectivity. This vinylation represents a new C(sp(3))-C(sp(2)) bond-forming reaction of high synthetic potential.
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