Rhodium(iii)-catalyzed synthesis of 3-trifluoromethylindanones from N-methoxybenzamides via C–H activation and Claisen/retro-Claisen reaction
Literature Information
Publication Date
2020-05-09
DOI
10.1039/D0QO00330A
Impact Factor
5.281
Authors
Bharatkumar Chaudhary, Neeraj Kulkarni, Satyasheel Sharma
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-Methyl-2-propanyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate
CAS Number:
154026-93-4
Molecular Formula:
C10H19ClO4
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