Base-catalyzed cross coupling of secondary alcohols and aryl-aldehydes with concomitant oxidation of alcohols to ketones: An alternative route for synthesis of the Claisen-Schmidt condensation products

• Published in: Tetrahedron letters 2017-07, Vol.58 (28), p.2761-2764
• Main Authors: Satrawala, Naveen, Sharma, Kamal N., Matsinha, Leah C., Maqeda, Latisa, Siangwata, Shepherd, Smith, Gregory S., Joshi, Raj K.
• Format: Article
• Language: English
• Subjects: Base catalyzed; Bis-(Benzylidene) alkanones; Claisen-Schmidt condensation; Cross coupling; One-pot synthesis
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2017.05.093

[Display omitted] •Base-catalyzed formation of α,α′-bis-(benzylidene) alkanones using sec-alcohols.•Alternative route for Claisen-Schmidt condensation products without using alkanones.•C–C cross coupling of sec-alcohols and aryl-aldehydes with no use of transition metal catalyst or additives. Base-catalyzed C–C cross coupling of secondary alcohols and aryl-aldehydes was achieved, when an alcoholic solution of an aryl-aldehyde was stirred under reflux for 45h in the presence of a catalytic (20mol%) amount of K2CO3. The consistent formation of α,α′-bis-(benzylidene) alkanones was obtained in moderate to good yields using various secondary alcohols and substituted aryl-aldehydes. Herein, α,α′-bis-(benzylidene)alkanones, which are the classical products of Claisen-Schmidt (cross aldol) condensation, have been synthesized via an alternative strategy using secondary alcohols. Bis-(benzylidene) alkanones are an integral part of various drug regimes and the production of bis-(benzylidene) alkanones without using any precious metal is a major outcome of the present reaction.