Direct Photoinduced Electron Transfer from Excited State of Rhodamine B for Carbon-Radical Generation

Eito Yoshioka; Shigeru Kohtani; Takahisa Jichu; Takuya Fukazawa; Toyokazu Nagai; Yoshiji Takemoto; Hideto Miyabe

doi:10.1055/s-0034-1379699

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(02): 265-270
DOI: 10.1055/s-0034-1379699

letter

Direct Photoinduced Electron Transfer from Excited State of Rhodamine B for Carbon-Radical Generation

Eito Yoshioka

^aSchool of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe, 650-8530, Japan eMail: kohtani@huhs.ac.jp eMail: miyabe@huhs.ac.jp

,

Shigeru Kohtani*

^aSchool of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe, 650-8530, Japan eMail: kohtani@huhs.ac.jp eMail: miyabe@huhs.ac.jp

,

Takahisa Jichu

^aSchool of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe, 650-8530, Japan eMail: kohtani@huhs.ac.jp eMail: miyabe@huhs.ac.jp

,

Takuya Fukazawa

^aSchool of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe, 650-8530, Japan eMail: kohtani@huhs.ac.jp eMail: miyabe@huhs.ac.jp

,

Toyokazu Nagai

^aSchool of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe, 650-8530, Japan eMail: kohtani@huhs.ac.jp eMail: miyabe@huhs.ac.jp

,

Yoshiji Takemoto

^bGraduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan

,

Hideto Miyabe*

^aSchool of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe, 650-8530, Japan eMail: kohtani@huhs.ac.jp eMail: miyabe@huhs.ac.jp

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Abstract

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Abstract

The photoinduced electron transfer (PIET) from the excited singlet state (S ₁) of rhodamine B to i-C₃F₇I smoothly proceeded in the presence of water. This process was supported by the fluorescence quenching of rhodamine B with addition of i-C₃F₇I in ethanol. The present method was applied to the atom-transfer radical reaction involving the cyclization step.

Key words

radical reaction - cyclization - photochemistry - alkyl halides - fluorine

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Referenzen

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17 General Procedure: A suspension of substrate in H₂O (10 mL) was degassed using three pump–thaw cycles under argon atmosphere at 0 °C. To this suspension were added (i-Pr)₂NEt (192 μL, 1.10 mmol), rhodamine B (24 mg, 0.050 mmol), and i-C₃F₇I (705 μL, 5.00 mmol) at r.t. The stirring reaction mixture was irradiated with white LED lamp (1000 lm) at r.t. After 0.5–1 h, the reaction mixture was concentrated under reduced pressure. Rough purification of the residue by flash silica gel column chromatography afforded the products as a mixture of isomers. The ratio of products was determined by ¹H NMR analysis of the mixture. Second purification of the mixture by flash silica gel column chromatography or preparative TLC afforded the isolated isomers. 1-Methoxy-4-[6,7,7,7-tetrafluoro-4-iodo-6-(trifluoromethyl)hepat-1-yl]benzene (2): Colorless oil. IR (KBr): 2937, 2837, 1612, 1513, 1462 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 7.09 (2 H, br dt, J = 8.7, 2.5 Hz), 6.84 (2 H, br dt, J = 8.7, 2.5 Hz), 4.36–4.30 (1 H, m), 3.79 (3 H, s), 2.96–2.75 (2 H, m), 2.67–2.51 (2 H, m), 1.87–1.66 (4 H, m). ¹³C NMR (101 MHz, CDCl₃): δ = 157.9, 133.4, 129.2, 120.7 (qd, J = 288, 28 Hz), 120.4 (qd, J = 288, 29 Hz), 113.8, 91.9 (dsept, J = 210, 32 Hz), 55.2, 40.3 (d, J = 2 Hz), 39.6 (d, J = 18 Hz), 33.7, 31.6, 22.3. ¹⁹F NMR (376 MHz, CDCl₃): δ = –76.5 (3 F, quin, J = 9 Hz), –7.8 (3 F, br quin, J = 9 Hz), –186.1 (1 F, m). HRMS (ESI⁺): m/z calcd for C₁₅H₁₆F₇IONa [M + Na⁺]: 495.0026; found: 495.0042.
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