Excited-state tris(pentafluorophenyl)borane as a strong single-electron oxidant: Photophysical properties and catalysis

• Published in: Journal of photochemistry and photobiology Vol. 18; p. 100206
• Main Authors: Aramaki, Yoshitaka, Uchida, Yuki, Ishikawa, Ryo, Ooi, Takashi
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-12-2023; Elsevier
• Subjects: Borane; Carbon-carbon bond formation; Photooxidant; Radical cation; Transient absorption spectroscopy; Photooxidant; Borane; Radical cation; Carbon-carbon bond formation; Transient absorption spectroscopy
• ISSN: 2666-4690; 2666-4690
• DOI: 10.1016/j.jpap.2023.100206

The photophysical properties and photocatalysis of tris(pentafluorophenyl)borane [B(C6F5)3], known as a strong Lewis acid, were revealed. The excited-state B(C6F5)3 exerts single-electron oxidation capability with an oxidation potential (Ered* = 2.02 V vs SCE) close to those of electronically unbiased toluene derivatives (Eox = 2.01 to 2.29 V). This property was experimentally proven by the direct observation of the radical cation of the toluene dimer by the transient absorption spectroscopy of a mixture of B(C6F5)3 and toluene. In cooperation with a suitable Brønsted base catalyst, B(C6F5)3 catalytically generated benzylic radicals from toluene derivatives under photoirradiation for subsequent carbon-carbon bond-forming reactions.
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