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DOI: 10.1055/s-2006-949640
A Novel Silver Iodide Catalyzed Sonogashira Coupling Reaction
Publication History
Publication Date:
24 August 2006 (online)
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Abstract
A novel and efficient Ag-catalyzed Sonogashira coupling reaction has been developed. Terminal alkynes couple with aryl iodides and aryl bromides in the presence of silver iodide, triphenylphosphine and potassium carbonate to afford the corresponding cross-coupling products in high yields.
Key words
silver iodide - Sonogashira coupling reactions - terminal alkynes - aryl iodides - aryl bromides
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It should be noted that the copper-free Sonogashira coupling reactions are representative and not comprehensive in this paper.
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References and Notes
The unique Sonogashira coupling products were characterized by mp, 1H NMR and 13C NMR, and MS.
(4-Acetylphenyl)phenylacetylene: mp 95-96 °C (Lit.24 94-96 °C). 1H NMR (250 MHz, CDCl3): δ = 7.91 (d, J = 8.41 Hz, 2 H), 7.58 (d, J = 8.41 Hz, 2 H), 7.52-7.54 (m, 2 H), 7.33-7.36 (m, 3 H), 2.57 (s, 3 H). 13C NMR (62.5 MHz, CDCl3): δ = 197.1, 136.1, 131.7, 131.6, 128.7, 128.4, 128.2, 128.1, 122.6, 92.6, 88.6, 26.5. MS (relative intensity, %): m/z = 220 (60) [M+], 205 (100), 176 (48), 151 (18), 102 (10), 88 (19).
(4-Cyanophenyl)phenylacetylene: mp 109-110 °C (Lit.25 108.5-109.5 °C). 1H NMR (300 MHz, CDCl3): δ = 7.59-7.66 (m, 4 H), 7.53-7.57 (m, 2 H), 7.36-7.40 (m, 3 H). 13C NMR (75 MHz, CDCl3): δ = 132.0 (2 × C), 131.8, 129.1, 128.5, 128.2, 122.2, 118.5, 111.4, 93.7, 87.7. MS: (relative intensity, %): m/z = 203 (100) [M+], 176 (8), 151 (5), 75 (5).
(3-Cyanophenyl)phenylacetylene: mp 69-71 °C (Lit.25 70-71 °C). 1H NMR (300 MHz, CDCl3): δ = 7.79 (t, J = 1.50 Hz, 1 H), 7.73 (dt, J = 1.50, 7.80 Hz, 1 H), 7.59 (dt, J = 1.50, 7.80 Hz, 1 H), 7.52-7.55 (m, 2 H), 7.45 (t, J = 7.80 Hz, 1 H), 7.35-7.39 (m, 3 H). 13C NMR (75 MHz, CDCl3): δ = 135.6, 134.8, 131.7, 131.3, 129.2, 128.9, 128.4, 124.8, 122.2, 118.0, 112.8, 91.7, 86.8. MS (relative intensity, %): m/z = 203 (100) [M+], 176 (7), 151 (5), 75 (5).