Transition Metal‐Free Stereoselective α‐Vinylation of Cyclic Ketones with Arylacetylenes in the Superbasic Catalytic Triad Potassium Hydroxide/ tert ‐Butyl Alcohol/Dimethyl Sulfoxide | Zendy

Trofimov Boris A. | Zendy; Schmidt Elena Yu. | Zendy; Zoridezhda V. | Zendy; Ivanova Elena V. | Zendy; Ushakov Igor' A. | Zendy; Mikhaleva Al'bina I. | Zendy

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Transition Metal‐Free Stereoselective α‐Vinylation of Cyclic Ketones with Arylacetylenes in the Superbasic Catalytic Triad Potassium Hydroxide/ tert ‐Butyl Alcohol/Dimethyl Sulfoxide

Author(s) -

Trofimov Boris A.,

Schmidt Elena Yu.,

Zoridezhda V.,

Ivanova Elena V.,

Ushakov Igor' A.,

Mikhaleva Al'bina I.

Publication year - 2012

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201200210

Subject(s) - chemistry , potassium hydroxide , catalysis , alcohol , medicinal chemistry , dimethyl sulfoxide , stereoselectivity , transition metal , sulfoxide , triad (sociology) , yield (engineering) , potassium , alcohol oxidation , organic chemistry , psychology , materials science , psychoanalysis , metallurgy

A stereoselective α‐vinylation of cycloaliphatic ketones with arylacetylenes under the transition metal‐free conditions has been developed. The reaction is promoted by the superbasic catalytic triad potassium hydroxide/ tert ‐butyl alcohol/dimethyl sulfoxide (80–110 °C, 1–2 h) to afford mainly ( E )‐β,γ‐ethylenic ketones, their ( E )‐α,β‐isomers being minor products, in up to 83% total yield.

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