Synlett 2015; 26(02): 265-270
DOI: 10.1055/s-0034-1379699
letter
© Georg Thieme Verlag Stuttgart · New York

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

Eito Yoshioka
a  School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe, 650-8530, Japan   Email: [email protected]   Email: [email protected]
,
Shigeru Kohtani*
a  School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe, 650-8530, Japan   Email: [email protected]   Email: [email protected]
,
Takahisa Jichu
a  School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe, 650-8530, Japan   Email: [email protected]   Email: [email protected]
,
Takuya Fukazawa
a  School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe, 650-8530, Japan   Email: [email protected]   Email: [email protected]
,
Toyokazu Nagai
a  School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe, 650-8530, Japan   Email: [email protected]   Email: [email protected]
,
Yoshiji Takemoto
b  Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
,
Hideto Miyabe*
a  School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe, 650-8530, Japan   Email: [email protected]   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 01 October 2014

Accepted after revision: 09 November 2014

Publication Date:
09 December 2014 (online)


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.

Supporting Information

 
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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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