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Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD^®/Olah's reagent under solvent-free conditions.

ABSTRACT: A new protocol enabling the formation of trifluoromethyl compounds from acyl fluorides has been developed. The combination of FLUOLEAD^® and Olah's reagent in solvent-free conditions at 70 °C initiated the significant deoxyfluorination of the acyl fluorides and resulted in the corresponding trifluoromethyl products with high yields (up to 99%). This strategy showed a great tolerance for various acyl fluorides containing aryloyl, (heteroaryl)oyl, or aliphatic acyl moieties, providing good to excellent yields of the trifluoromethyl products. Synthetic drug-like molecules were also transformed into the corresponding trifluoromethyl compounds under the same reaction conditions. A reaction mechanism is proposed.

SUBMITTER: Liang Y

PROVIDER: S-EPMC7753111 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah's reagent under solvent-free conditions.

Liang Yumeng Y Taya Akihito A Zhao Zhengyu Z Saito Norimichi N Shibata Norio N

Beilstein journal of organic chemistry 20201214

A new protocol enabling the formation of trifluoromethyl compounds from acyl fluorides has been developed. The combination of FLUOLEAD® and Olah's reagent in solvent-free conditions at 70 °C initiated the significant deoxyfluorination of the acyl fluorides and resulted in the corresponding trifluoromethyl products with high yields (up to 99%). This strategy showed a great tolerance for various acyl fluorides containing aryloyl, (heteroaryl)oyl, or aliphatic acyl moieties, providing go ...[more]

PMID: 33414852

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