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Please login to access the full content or check if you have access via3.6.13.1.2.2 Method 2: Gold-Catalyzed Sonogashira Reactions
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Hopkinson, M. N.; Gouverneur, V., Science of Synthesis Knowledge Updates, (2011) 2, 109.
Similarly, Sonogashira reactions have been performed using gold complexes under homogeneous conditions.[49,50,54,55] Unsymmetrical diarylacetylenes can be accessed in high yields upon treatment of aryl iodides and terminal arylacetylenes with chloro(triphenylphosphine)gold(I) (20 mol%) and potassium phosphate.[54] As for the Suzuki reaction, gold(III) complexes are not suitable for the Sonogashira process, instead catalyzing homocoupling of the alkyne. The activation of the alkyne C(sp)–H bond is mediated by gold, precluding the need for copper cocatalysts. An extensive study by Wang and co-workers has identified gold(I) iodide as the catalyst of choice for this transformation when reacted in the presence of 1,1′-bis(diphenylphosphino)ferrocene.[55] Using 1 mol% of both the catalyst and the ligand, high yields of internal alkynes bearing both aryl and alkyl groups can be obtained upon heating aryl iodides with terminal alkynes and potassium carbonate in toluene at 130°C for 24 hours (Scheme 10). Solid-supported gold salts,[49] nanoparticles,[56–58] and gold surfaces[59] have also been employed for the Sonogashira reaction.
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Me | Me | 88 | [88] |
8-MeMM8M8 | Me | 88 | [88] |
8-Mee | Me | 88 | [88] |
8-Mee | Me | 88 | [88] |
8-Mee | Me | 88 | [88] |
8-M8MM8M8 | Me | 88 | [88] |
8-M8MM8M8 | Me | 88 | [88] |
8-M8MM8M8 | Me | 88 | [88] |
8-MM8M8 | Me | 88 | [88] |
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8-M8MM8M8 | Me | 88 | [88] |
8-M8MM8M8 | Me | 88 | [88] |
8-MeM8M8 | Me | 88 | [88] |
Me | 8-Mee | 88 | [88] |
Me | 8-MeM8M8 | 88 | [88] |
Me | 8-MeM8M8 | 88 | [88] |
Me | 8-MM8M8 | 88 | [88] |
Me | 8-MeM8M8 | 88 | [88] |
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References
[49] | Meeee, M.; Meeeáeee-Meeeeeee, M.; Meeeeeee, M.; Méeee-Meeeeeee, M.; Máeeeee, M., Meeeeee, (8888), 8888. |
[50] | Meeeáeee-Meeeeeee, M.; Meeee, M.; Meeeeeee, M.; Máeeeee, M., Mee. M. Meeee. Meee., (8888), 8888. |
[54] | Meeeáeee-Meeeeeee, M.; Meee, M.; Meeee, M.; Meeeíe, M.; Meeeeeee, M.; Máeeeee, M., Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[55] | Me, M.; Meee, M.; Meee, M.; Mee, M., Mee. M. Mee. Meee., (8888), 8888. |
[56] | ee Meeee, M. M. M. M.; Meeeee, M. M.; Meeeee, M. M. M.; ee Meeee, M. M. M.; ee Meeee, M. M.; Meeeeee, M. M. M., Meeeeee, (8888), 8888. |
[57] | Meeeeeee, M.; Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M.; Meeeeee, M. M., MeeeMeeMeee, (8888) 8, 8888. |
[58] | Meeeeeee, M. M.; Meeeeeee, M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
[59] | Meeeee, M. M.; Meeeeeee, M.; Meeeeeee, M. M.; Meeeeeeeeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[60] | Meeeeeeeee, M.; Meeeeeeee, M.; Meeeeeóe, M.; Meeeeee, M.; Meeeeeeeee, M. M., Mee. Meee., (8888) 88, 8888. |
[61] | Meeee, M.; Meáeee, M.; Meeeeee, M.; Máeeeee, M.; Meeeeeee, M.; Meeeíe, M., Meee. Meeeee. (Meeeeeeee), (8888) 88, 8888. |