Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids

Min Jiang; Haijun Yang; Yunhe Jin; Lunyu Ou; Hua Fu

doi:10.1055/s-0037-1610188

Synlett, Table of Contents

Synlett 2018; 29(12): 1572-1577
DOI: 10.1055/s-0037-1610188

letter

Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids

Min Jiang

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China Email: fuhua@mail.tsinghua.edu.cn

,

Haijun Yang

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China Email: fuhua@mail.tsinghua.edu.cn

,

Yunhe Jin

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China Email: fuhua@mail.tsinghua.edu.cn

,

Lunyu Ou

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China Email: fuhua@mail.tsinghua.edu.cn

,

Hua Fu *

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China Email: fuhua@mail.tsinghua.edu.cn

› Author Affiliations

Abstract

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Abstract

A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.

Key words

visible-light - photoredox - aromatic carboxylic acids - decarboxylation - iodination

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References

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24 General procedures for the iodination of aromatic carboxylic acids General procedure A: To a 15 mL test tube with septum, Cs₂CO₃ (0.6 mmol, 195 mg), aromatic carboxylic acid (1; 0.3 mmol), [Ir(dF(CF₃)ppy)₂dtbbpy]PF₆ (D; 6 μmmol, 6.7 mg), N-iodosuccinimide (NIS; 0.9 mmol, 202.5 mg), and I₂ (15 μmol, 5 mol%) were added. The tube was evacuated and backfilled with argon three times, and then 3 mL of anhydrous 1,2-dichloroethane (DCE) was added through a syringe under argon. The tube was sealed with Parafilm M^® and placed in an oil bath with a contact thermometer, and the reaction was carried out at 50 °C under irradiation with 6 × 5 W blue LEDs (λ_max = 455 nm). After 24 or 36 h, the resulting mixture was filtered through a 2 cm thick pad of silica, and the silica was washed with dichloromethane (50 mL). The filtrate was collected and the solvent was removed in vacuo. The crude residue was purified by silica gel flash column chromatography to provide the target product 2 (Note: The reaction was very sensitive to moisture, and the yields sharply decreased to less than 5% when 0.01 equivalent of H₂O was added to the reaction system).General procedure B: To a 15 mL test tube with septum, Cs₂CO₃ (0.6 mmol, 195 mg), aromatic carboxylic acid (1; 0.3 mmol), [Ir(dF(CF₃)ppy)₂dtbbpy]PF₆ (D; 6 μmol, 6.7 mg), NIS (1.5 mmol, 337.5 mg) and I₂ (60 μmol, 20 mol%) were added. The tube was evacuated and backfilled with argon three times, and then 3 mL of anhydrous DCE was added through a syringe under argon. The tube was sealed with Parafilm M® and placed in an oil bath with a contact thermometer, and the reaction was carried out at 50 °C under irradiation with 6 × 5 W blue LEDs (λ_max = 455 nm). After 24 h or 36 h, the resulting mixture was filtered through a 2 cm thick pad of silica, and the silica was washed with CH₂Cl₂ (50 mL). The filtrate was collected and the solvent was removed in vacuo. The crude residue was purified by silica gel flash column chromatography to provide the target product 2 (Note: The reaction was very sensitive to moisture, and the yields sharply decreased to less than 5% when 0.01 equivalent of H₂O was added to the reaction system).General procedure C: To a 15 mL test tube with septum, Cs₂CO₃ (0.6 mmol, 195 mg), aromatic carboxylic acid (1; 0.3 mmol), [Ir(dF(CF₃)ppy)₂dtbbpy]PF₆ (D; 6 μmol, 6.7 mg), NIS (1.5 mmol, 337.5 mg) and I₂ (60 μmol, 20 mol%) were added. The tube was evacuated and backfilled with argon for times, and then 3 mL of anhydrous CH₃CN was added through a syringe under argon. The tube was sealed with Parafilm M® and placed in an oil bath with a contact thermometer, and the reaction was carried out at 50 °C under irradiation with 6 × 5 W blue LEDs (λ_max = 455 nm). After 24 h, the resulting mixture was filtered through a 2 cm thick pad of silica, and the silica was washed with CH₂Cl₂ (50 mL). The filtrate was collected and the solvent was removed in vacuo. The crude residue was purified by silica gel flash column chromatography to provide the target product 2 (Note: The reaction was very sensitive to moisture, and the yields sharply decreased to less than 5% when 0.01 equivalent of H₂O was added to the reaction system).Three representative examples are shown as follows:1-Iodo-3-methoxybenzene (2f)²⁵Eluent: pentane/diethyl ether 50:1, the solvent was removed under reduced pressure. Yield: 52.7 mg (75%) by following general procedure A. Colorless oil. ¹H NMR (CDCl₃, 400 MHz): δ = 7.29 (d, J = 8.24 Hz, 1 H), 7.26 (s, 1 H), 7.0 (t, J = 8.24 Hz, 1 H), 6.87 (d, J = 8.70 Hz, 1 H), 3.78 (s, 3 H). ¹³C NMR (CDCl₃, 100 MHz): δ = 160.2, 130.9, 129.9, 123.1, 113.8, 94.5, 55.5. EI-MS: M⁺ m/z 234.Methyl 4-iodobenzoate (2s)²⁵Eluent: pentane/diethyl ether 50:1, the solvent was removed under reduced pressure. Yield: 59.7 mg (76%) by following general procedure B. White solid; mp 113–115 °C. ¹H NMR (CDCl₃, 400 MHz): δ = 7.79 (d, J = 8.24 Hz, 2 H), 7.64 (d, J = 8.24 Hz, 2 H), 3.95 (s, 3 H). ¹³C NMR (CDCl₃, 100 MHz): δ = 167.0, 137.2, 130.6, 129.2, 100.4, 52.2. EI-MS: m/z = 262 [M⁺].3-Iodopyridine (2ab)²⁶Eluent: pentane/diethyl ether 5:1, the solvent was removed at 0 °C under reduced pressure. Yield: 45.5 mg (65%) by following general procedure C. Yellow oil. ¹H NMR (CDCl₃, 400 MHz): δ = 8.86 (s, 1 H), 8.79 (d, J = 5.04 Hz, 1 H), 7.94 (d, J = 8.24 Hz, 1 H), 7.42 (t, J = 6.87 Hz, 1 H). ¹³C NMR (CDCl₃, 100 MHz): δ = 146.7, 144.3, 139.6, 130.2, 129.4, 128.9, 128.2, 120.1, 127.7, 98.8. EI-MS: m/z = 205 [M⁺]
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