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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Eosin Y Catalyzed Photochemical Synthesis of Arylated Phenothiazones
Bhawana Nagar1, Sarban Kumar Yadav1, Naiwrit Karmodak1
1Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Dadri, UP 201314, India.
Abstract:
In the presence of Eosin Y (EY), the synthesis of substituted phenothiazones was carried out efficiently using various substituted 2-aminothiophenol, diazonium salts, and 1,4-napthaquinones (1,4-NQ) at room temperature (RT) (condition: green LED of 525 nm, 44 W; reaction time: 8 h, isolated yield: 68-90%). A fluorescence quenching experiment and density functional theory (DFT) calculations suggested that the triplet photoexcited state of EY (EY*; τT = 320 ± 10 ns) converts to EY+• via oxidative quenching by ArN2 + (-1.11 V vs SCE for EY* to EY+•) initially. Thiyl and aryl radicals were captured as TEMPO adducts in high-resolution mass spectroscopy (HRMS). The reaction was not inhibited by the addition of a singlet oxygen quencher such as 1,4-diazobicyclo [2.2.2] octane (DABCO), which suggests that singlet oxygen is not participated.
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