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Synthesis of α-Difluoromethyl aryl ketones through a photoredox difluoromethylation of enol silanes

Synthesis of α-Difluoromethyl aryl ketones through a photoredox difluoromethylation of enol silanes

Selmi-Higashi, Elias, Zhang, Jinlei, Cambeiro, Xacobe C. ORCID: 0000-0002-7365-7201 and Arseniyadis, Stellios ORCID: 0000-0001-6831-2631 (2021) Synthesis of α-Difluoromethyl aryl ketones through a photoredox difluoromethylation of enol silanes. Organic Letters, 23 (11). pp. 4239-4243. ISSN 1523-7060 (Print), 1523-7052 (Online) (doi:https://doi.org/10.1021/acs.orglett.1c01177)

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Abstract

We report here an efficient and highly straightforward access to α-difluoromethylated ketones through a visible light-mediated difluoromethylation of readily available enol silanes. The method, which takes advantage of the polyvalence of Hu’s reagent, N-tosyl-S-difluoromethyl-S-phenylsulfoximine, used here as a CHF2 radical precursor under catalytic photoredox conditions, is practical, scalable, and provides the corresponding α-CHF2 ketones in good to excellent yields.

Item Type: Article
Uncontrolled Keywords: Ethers, Transfer reactions, Catalysts, Aromatic compounds, Ketones
Subjects: T Technology > T Technology (General)
T Technology > TA Engineering (General). Civil engineering (General)
Faculty / Department / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Last Modified: 20 Jun 2021 23:31
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
Selected for GREAT 2019: None
Selected for REF2021: None
URI: http://gala.gre.ac.uk/id/eprint/33096

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