Push-pull Benzophenone-type Photoredox Catalyst for C(sp2)-C(sp3) Cross-coupling Reactions
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4-Methoxy-4'-trifluoromethylbenzophenone (1) is a benzophenone derivative bearing an electron-withdrawing trifluoromethyl group and an electron-donating methoxy group. Under light irradiation, benzophenone derivatives are excited to the triplet state and generate biradical species, allowing them to act as photoredox catalysts for energy transfer (ET), single electron transfer (SET), and hydrogen atom transfer (HAT). Excitation of benzophenone typically requires high-energy UV light, which can easily degrade substrates. Thanks to its push-pull structure, the absorption of 1 is shifted to a longer wavelength, so reactions can proceed under milder conditions. Compound 1 has been reported as a catalyst for C(sp2)-C(sp3) cross-coupling reactions. For example, under fluorescent light irradiation, the cross-coupling between aryl bromides and saturated heterocycles proceeds in the presence of catalytic amounts of 1, Ni(acac)2 and 6,6'-di-3-picolyl, along with stoichiometric amounts of sodium carbonate.¹) Compound 1 can also generate silyl radicals by HAT from tris(trimethylsilyl)silane. Silyl radicals can further generate alkyl radicals by halogen atom transfer (XAT), enabling reductive cross-coupling between aryl bromides and alkyl bromides.²)
Related products
- TCI T4165 6185-76-8 (4-Methoxyphenyl)[4-(trifluoromethyl)phenyl]methanone
- TCI N0096 120156-44-7 Bis(2,4-pentanedionato)nickel(II) Hydrate
- TCI S0560 497-19-8 Sodium Carbonate
References
- sp3 C-H Arylation and Alkylation Enabled by the Synergy of Triplet Excited Ketones and Nickel Catalysts. Y. Shen, Y. Gu, R. Martin, J. Am. Chem. Soc. 2018, 140, 12200.
- The Merger of Benzophenone HAT Photocatalysis and Silyl Radical-Induced XAT Enables Both Nickel-Catalyzed Cross-Electrophile Coupling and 1,2-Dicarbofunctionalization of Olefins. A. Luridiana et al., T. Noel, ACS Catal. 2022, 12, 11216.
Source
- TCI Product Highlights: www.tcichemicals.com/ID/en/product/tci-topics/ProductHighlights_20240527
- TCI product page T4165: tcichemicals.com/ID/en/p/T4165
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