Room-Temperature Arylation of Arenes and Heteroarenes with Diaryl­iodonium Salts by Photoredox Catalysis

Yu-Xia Liu; Dong Xue; Jia-Di Wang; Cong-Jun Zhao; Qing-Zhu Zou; Chao Wang; Jianliang Xiao

doi:10.1055/s-0032-1318155

Synlett, Table of Contents

Synlett 2013; 24(4): 507-513
DOI: 10.1055/s-0032-1318155

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Room-Temperature Arylation of Arenes and Heteroarenes with Diaryliodonium Salts by Photoredox Catalysis

Yu-Xia Liu

^aKey Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

,

Dong Xue*

^aKey Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

,

Jia-Di Wang

^aKey Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

,

Cong-Jun Zhao

^aKey Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

,

Qing-Zhu Zou

^aKey Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

,

Chao Wang

^aKey Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

,

Jianliang Xiao*

^aKey Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China Fax: +86(29)81530727 Email: xuedong_welcome@snnu.edu.cn

^bDepartment of Chemistry, Liverpool Centre for Materials and Catalysis, University of Liverpool, Liverpool, L69 7ZD, UK Email: J.Xiao@liverpool.ac.uk

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Abstract

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Abstract

Aryl radicals produced by irradiation of diaryliodonium salts with visible light under the catalysis of [Ru(bpy)₃]²⁺ undergo coupling with a wide range of arenes and heteroarenes, affording various biaryls through direct C–H arylation at room temperature.

Key words

arenes - heteroarenes - visible light - aryl radicals - ruthenium

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References

References and Notes

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16 General Procedure for the Direct Arylation of Arenes and Heteroarenes with Diaryliodonium Salts Method AA flame dried 10 mL Schlenk tube was equipped with a rubber septum and magnetic stir bar and was charged with tris(2,2′-bipyridyl)ruthenium(II) chloride hexahydrate (3 mg, 0.004 mmol, 0.01 equiv), diarylionium salts (0.4 mmol, 1.0 equiv), arenes or heteroarenes (20 mmol, 50 equiv), and MeCN (3 mL). The mixture was degassed by the freeze-pump-thaw procedure with Ar, and then the Schlenk tube was placed at a distance of 10 cm from a 3w Blue LED bulb. After stirring at 25 °C for 12 h, the solvent was removed under reduced pressure, and the residue purified by flash chromatography to afford the product. The identity and purity of the product was confirmed by ¹H NMR and ¹³C NMR spectroscopy and MS or HRMS.Method BThis method is the same as method A except that a smaller amount of arene or heteroarene (4 mmol, 10 equiv) was used. The method was used mainly for substrates that did not fully dissolve under the conditions in method A.1-Methyl-2-Phenyl-1H-pyrrole (3a)Compound 3a was obtained following the method A. White solid, mp 43–44 °C; R_f = 0.2 (PE–CH₂Cl₂ = 10:1); yield 87% (63 mg). ¹H NMR (400 MHz, CDCl₃): δ = 7.43–7.40 (m, 4 H), 7.34–7.31 (m, 1 H), 6.75 (s, 1 H), 6.27–6.24 (m, 2 H), 3.69 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 134.7, 133.5, 128.8, 128.4, 126.7, 123.7, 108.7, 107.8, 35.1. MS (EI): m/z = 158.1 [M + H]⁺.1-Methyl-2-(4-Fluorophenyl)-1H-pyrrole (3b)Compound 3b was obtained following the method A. White solid, mp 64 °C; R_f = 0.2 (PE–CH₂Cl₂ = 20:1); yield 91% (64 mg). ¹H NMR (400 MHz, CDCl₃): δ = 7.39–7.36 (m, 2 H), 7.13–7.09 (m, 2 H), 6.73 (d, J = 2.0, 1 H), 6.23–6.22 (m, 2 H), 3.65 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 162.0 (d, J _C–F = 245.8 Hz), 133.6, 130.3 (d, J _C–F = 8.8 Hz), 129.5 (d, J _C–F = 3.3 Hz), 123.6, 115.3 (d, J _C–F = 21.3 Hz), 108.7, 107.8, 34.9. IR (KBr, plate): ν = 3429, 2950, 2923, 1719, 1609, 1494, 1437, 1279, 859, 779, 705 cm^–1. ESI-HRMS: m/z calcd for C₁₁H₁₁FN [M + H]⁺: 176.0876; found: 176.0866.1-Methyl-2-(2-Fluorophenyl)-1H-pyrrole (3c)Compound 3c was obtained following the method A. Colorless oil; R_f = 0.2 (PE–CH₂Cl₂ = 20:1); yield 91% (64 mg). ¹H NMR (400 MHz, CDCl₃): δ = 7.38–7.32 (m, 2 H), 7.19–7.12 (m, 2 H), 6.78 (t, J = 2.0 Hz, 1 H), 6.25 (d, J = 2.0 Hz, 2 H), 3.58 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 160.0 (d, J _C–F = 245.0 Hz), 132.1 (d, J _C–F = 3.1 Hz), 129.2 (d, J _C–F = 8.1 Hz), 128.2, 124.1 (d, J _C–F = 3.4 Hz), 123.5, 121.2 (d, J _C–F = 15.3 Hz), 115.7 (d, J _C–F = 22.5 Hz), 109.9, 107.9, 34.7. ESI-HRMS: m/z calcd for C₁₁H₁₁FN [M + H]⁺: 176.0876; found: 176.0871.

Supplementary Material

Supporting Information

Room-Temperature Arylation of Arenes and Heteroarenes with Diaryl­iodonium Salts by Photoredox Catalysis

Room-Temperature Arylation of Arenes and Heteroarenes with Diaryliodonium Salts by Photoredox Catalysis