Synthesis of α‑Trifluoromethylated Ketones from α,β-Unsaturated Ketones via Catecholboron Enolates

Herein, we report a protocol for the synthesis of α-trifluoromethylated ketones through trifluoromethylation of the corresponding catecholboron enolates of α,β-unsaturated ketones. The reaction of the 1,4-hydroborated product of enones with the Togni II reagent affords the α-trifluoromethylated keto...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-08, Vol.89 (16), p.11480-11486
Main Authors: Keerthika, K., S, Bazil Muhammed, Geetharani, K.
Format: Article
Language:English
Subjects:
catalysts
chalcones
organic chemistry
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Summary:Herein, we report a protocol for the synthesis of α-trifluoromethylated ketones through trifluoromethylation of the corresponding catecholboron enolates of α,β-unsaturated ketones. The reaction of the 1,4-hydroborated product of enones with the Togni II reagent affords the α-trifluoromethylated ketones without any catalyst or additive. Moreover, the protocol has been employed on a series of α,β-unsaturated ketones, including chalcones, substrate-bearing heterocycles, and bioactive molecules. Mechanistic studies suggest the involvement of a trifluoromethyl radical during the reaction.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01159