期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 20, 页码 13220-13227出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01999
关键词
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资金
- JSPS (KAKENHI) [19H02711, 17J07953, JP16H06038, 20K20365, JP18H04241]
- JST CREST [JPMJCR18R4]
- Grants-in-Aid for Scientific Research [17J07953, 19H02711] Funding Source: KAKEN
Organic photoredox catalysis has become a useful tool for the development of metal-free radical reactions. Recently, we have reported that 1,4-bis(diphenylamino)naphthalene N serves as an efficient photoredox catalyst for radical monofluoromethylation with N-tosyl-S-monofluoromethyl-S-phenylsulfoximine 2. In this paper, we report the preparation and photoand electrochemical properties of (diarylamino)naphthalene derivatives, 1,4-bis(di(p-tert-butylphenyl)amino)naphthalene 1a, 1,5-bis(di(p-tert-butylphenyl)amino)naphthalene 1b, and 1-(di(p-tert-butylphenyl)amino)naphthalene) 1a, as supported by density functional theory (DFT) and time-dependent-DFT calculations. In addition, their performance of photocatalysis has been evaluated by means of methoxy-monofluoromethylation of aromatic alkenes. Laser flash photolysis shows that the fluorescence of la in the excited state is efficiently quenched by 2 (quenching rate constant k(q) = ca. 2 X 10(9) M-1 s(-1)). Transient absorption spectroscopic analyses reveal that the excited species of 1a in the presence of 2 starts decreasing in ca. 100 ps, suggesting the occurrence of fast electron-transfer processes. These results lead to the unconventional concept for the catalyst design, that is, long lifetime of the excited state is not always a requisite for efficient photoredox catalysts.
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