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

IF 3.261

Journal of Photochemistry and Photobiology Pub Date : 2023-08-29 DOI:10.1016/j.jpap.2023.100206

Yoshitaka Aramaki, Yuki Uchida, Ryo Ishikawa, Takashi Ooi

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Abstract

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 (E_red* = 2.02 V vs SCE) close to those of electronically unbiased toluene derivatives (E_ox = 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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激发态三(五氟苯基)硼烷作为强单电子氧化剂:光物理性质和催化

研究了强路易斯酸三(五氟苯基)硼烷[B(C6F5)3]的光物理性质和光催化作用。激发态B(C6F5)3具有单电子氧化能力，其氧化电位(Ered* = 2.02 V vs SCE)接近电子无偏甲苯衍生物的氧化电位(Eox = 2.01 ~ 2.29 V)。通过对B(C6F5)3和甲苯混合物的瞬态吸收光谱直接观察甲苯二聚体的自由基阳离子，实验证明了这一特性。在合适的Brønsted碱催化剂的作用下，B(C6F5)3在光照射下催化甲苯衍生物生成了苯自由基，用于随后的碳-碳成键反应。

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来源期刊

Journal of Photochemistry and Photobiology

CiteScore

4.10

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0.00%

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