Diversely Substituted Quinolines via Rhodium-Catalyzed Alkyne Hydroacylation
James D Neuhaus1, Sarah M Morrow1, Michael Brunavs2
1Department of Chemistry, University of Oxford, Chemistry Research Laboratory , Mansfield Road, Oxford, OX1 3TA, U.K.
Abstract:
The Rh-catalyzed hydroacylative union of aldehydes and o-alkynyl anilines leads to 2-aminophenyl enones, and onward to substituted quinolines. The mild reaction conditions employed in this chemistry result in a process that displays broad functional group tolerance, allowing the preparation of diversely substituted quinolines in high yields. Extension to the use of o-alkynyl nitro arenes as substrates leads to 2-nitrochalcones, from which both quinolines and quinoline N-oxides can be accessed.
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