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Synlett 2016; 27(10): 1602-1606
DOI: 10.1055/s-0035-1561404
DOI: 10.1055/s-0035-1561404
letter
Visible-Light-Mediated Facile Reductive Aromatization of Quinols
Weitere Informationen
Publikationsverlauf
Received: 30. Dezember 2015
Accepted after revision: 08. Februar 2016
Publikationsdatum:
09. März 2016 (online)
Abstract
A range of phenols bearing multiple useful functionalities at their meta positions were prepared from the corresponding quinols under the cooperative effects of visible light irradiation, Ru(bpy)3Cl2 photosensitizer, Hünig’s base, LiBF4, and MeCN solvent. The process involves visible-light-enabled photocatalytic cleavage of C–O bond as the strategic event.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561404.
- Supporting Information
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References and Notes
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- 9 General Procedure for Visible-Light-Mediated Facile Reductive Aromatization of Quinols: A flame-dried round-bottom flask (10 mL) was equipped with magnetic stirring bar and charged with quinol compound (0.1 mmol, 1.0 equiv), tris(2,2′-bipyridyl)ruthenium(II) chloride hexahydrate (0.005 mmol, 0.05 equiv), LiBF4 (0.2 mmol, 2.0 equiv) and MeCN (2.0 mL). To the mixture was then added amine (0.5 mmol, 5.0 equiv), and it was irradiated by a household bulb (45 W) under a balloon argon atmosphere at r.t. until the starting material disappeared from the TLC. The reaction mixture was filtrated through celite and washed with Et2O. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to afford the pure product. (Z)-3-(3-Hydroxy-1-phenylprop-1-en-1-yl)-4-methylphenol (4a): colorless liquid; yield: 23.3 mg (97%). 1H NMR (500 MHz, CDCl3): δ = 7.13–7.30 (m, 5 H), 7.02 (d, J = 8.2 Hz, 1 H), 6.75 (dd, J = 8.2, 2.7 Hz, 1 H), 6.62 (d, J = 2.7 Hz, 1 H), 6.29 (t, J = 6.9 Hz, 1 H), 4.27 (s, 2 H), 4.02 (d, J = 5.9 Hz, 2 H), 1.89 (s, 3 H). 13C NMR (126 MHz, CDCl3): δ = 153.76 (s), 143.13 (s), 139.95 (s), 139.30 (s), 131.35 (s), 128.35 (s), 128.18 (s), 127.59 (s), 126.70 (s), 126.46 (s), 116.64 (s), 114.83 (s), 60.84 (s), 18.59 (s). HRMS: m/z [M + Na+] calcd for C16H16NaO2: 263.1048; found: 263.1041. (Z)-2-(3-Hydroxy-1-phenylprop-1-en-1-yl)-[1,1′-biphenyl]-4-ol (4d): white solid; yield: 27.2 mg (90%). 1H NMR (500 MHz, MeOD): δ = 7.21 (d, J = 8.4 Hz, 1 H), 7.06–7.17 (m, 10 H), 6.89 (dd, J = 8.4, 2.6 Hz, 1 H), 6.69 (d, J = 2.6 Hz, 1 H), 6.06 (t, J = 6.4 Hz, 1 H), 4.00–4.14 (m, 1 H), 3.80 (dd, J = 13.2, 5.3 Hz, 1 H). 13C NMR (126 MHz, acetone): δ = 156.51 (s), 141.53 (s), 141.29 (s), 140.95 (s), 138.76 (s), 133.35 (s), 131.26 (s), 129.30 (s), 128.78 (s), 127.92 (s), 127.56 (s), 126.89 (s), 126.66 (s), 126.12 (s), 117.41 (s), 115.05 (s), 60.17 (s). HRMS: m/z [M + Na+] calcd for C21H18NaO2: 325.1204; found: 325.1200. (Z)-3-{1-([1,1′-Biphenyl]-4-yl)-3-hydroxyprop-1-en-1-yl}-4-methylphenol (4l): white solid; yield: 25.6 mg (81%). 1H NMR (500 MHz, CDCl3): δ = 7.53 (d, J = 7.4 Hz, 2 H), 7.44 (d, J = 8.3 Hz, 2 H), 7.39 (t, J = 7.6 Hz, 2 H), 7.32 (t, J = 7.3 Hz, 1 H), 7.25 (d, J = 8.3 Hz, 2 H), 7.05 (d, J = 8.3 Hz, 1 H), 6.78 (dd, J = 8.2, 2.6 Hz, 1 H), 6.67 (d, J = 2.6 Hz, 1 H), 6.36 (t, J = 6.9 Hz, 1 H), 3.98–4.10 (m, 2 H), 1.92 (s, 3 H). 13C NMR (126 MHz, CDCl3): δ = 153.85 (s), 143.02 (s), 140.50 (s), 140.33 (s), 139.09 (s), 138.79 (s), 131.44 (s), 128.79 (s), 128.14 (s), 127.35 (s), 127.03 (s), 126.92 (s), 126.87 (s), 126.27 (s), 116.58 (s), 114.98 (s), 60.78 (s), 18.68 (s). HRMS: m/z [M + Na+] calcd for C22H20NaO2: 339.1361; found: 339.1357. (Z)-3-[1-(3,4-Dimethylphenyl)-3-hydroxyprop-1-en-1-yl]-4-methylphenol (4o): colorless liquid; yield: 23.0 mg (86%). 1H NMR (400 MHz, CDCl3): δ = 6.99–7.13 (m, 3 H), 6.94 (d, J = 7.9 Hz, 1 H), 6.75 (dd, J = 8.2, 2.7 Hz, 1 H), 6.59 (d, J = 2.6 Hz, 1 H), 6.31 (t, J = 6.8 Hz, 1 H), 4.04 (d, J = 6.8 Hz, 2 H), 2.23 (s, 3 H), 2.21 (s, 3 H), 1.97 (s, 3 H). 13C NMR (101 MHz, CDCl3): δ = 153.5 (s), 142.9 (s), 138.9–139.5 (m), 137.5 (s), 136.4 (s), 136.2 (s), 131.2 (s), 129.6 (s), 128.2 (s), 127.5 (s), 125.7 (s), 124.0 (s), 116.5 (s), 114.5 (s), 60.9 (s), 19.8 (s), 19.4 (s), 18.6 (s). HRMS: m/z [M + Na+] calcd for C18H20NaO2: 291.1361; found: 291.1354.
For selected examples of Michael addition reactions of quinols, see:
For selected examples of Michael addition reactions of quinols, see:
For selected examples of reductive aromatization of quinols, see:
For selected recent reviews on photoredox catalysis, see:
For selected examples of visible-light-enabled photocatalytic cleavages of C–C and C–X bonds, see: