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

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发布日期 2020-05-09

DOI 10.1039/D0QO00330A

影响因子 5.281

作者

Bharatkumar Chaudhary, Neeraj Kulkarni, Satyasheel Sharma

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摘要

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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来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 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

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

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