Base-Catalyzed Stereoselective Vinylation of Ketones with Arylacetylenes: A New C(sp3)C(sp2) Bond-Forming Reaction

Alkylaryl‐ and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100 °C, 1 h) to give regio‐ and stereoselectively the (E)‐β‐γ‐ethylenic ketones ((E)‐3‐buten‐1‐ones) in 61–84 % yields and with approximately 100 % stereosele...

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Bibliographic Details
Published in:Chemistry : a European journal 2010-07, Vol.16 (28), p.8516-8521
Main Authors: Trofimov, Boris A., Schmidt, Elena Yu, Ushakov, Igor' A., Zorina, Nadezhda V., Skital'tseva, Elena V., Protsuk, Nadezhda I., Mikhaleva, Al'bina I.
Format: Article
Language:English
Subjects:
alkynes
Bonding
Chemistry
Condensing
CC bond formation
Ketones
Stereoselectivity
superbases
vinylation
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Summary:Alkylaryl‐ and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100 °C, 1 h) to give regio‐ and stereoselectively the (E)‐β‐γ‐ethylenic ketones ((E)‐3‐buten‐1‐ones) in 61–84 % yields and with approximately 100 % stereoselectivity. This vinylation represents a new C(sp3)C(sp2) bond‐forming reaction of high synthetic potential. A valuable vinylation! Previously unknown C‐vinylation of ketones occurs with high E stereoselectivity and excellent yields when alkylaryl‐ and alkylheteroarylketones are treated with arylacetylenes in the presence of KOH/DMSO at 100 °C. This represents a new C(sp3)C(sp2) bond‐forming reaction of wide scope (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201000227