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Rhodium(iii)-catalyzed synthesis of 3-trifluoromethylindanones from N-methoxybenzamides via C–H activation and Claisen/retro-Claisen reaction

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Abstract

A rhodium(III)-catalyzed reaction of N-methoxybenzamides as a directing group with β-trifluoromethyl-α,β-unsaturated ketones is reported. The reaction involved sp2 C–H activation, followed by the Claisen condensation involving a C–N bond cleavage to form 2-acyl-3-trifluoromethylindanone products. Furthermore, C2-unsubstituted 3-trifluoromethylindanone formation occurs through the trifluoroethanol-mediated retro-Claisen condensation reaction. This protocol is an efficient, straightforward route for the synthesis of 3-trifluoromethylindanone derivatives.

Graphical abstract: Rhodium(iii)-catalyzed synthesis of 3-trifluoromethylindanones from N-methoxybenzamides via C–H activation and Claisen/retro-Claisen reaction

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Article information


Submitted
13 Mar 2020
Accepted
08 May 2020
First published
09 May 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Rhodium(III)-catalyzed synthesis of 3-trifluoromethylindanones from N-methoxybenzamides via C–H activation and Claisen/retro-Claisen reaction

B. Chaudhary, N. Kulkarni and S. Sharma, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00330A

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