A Versatile Catalyst for the Sonogashira Coupling of Aryl Chlorides
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Aryl chlorides are suitable substrates for the Sonogashira coupling! By using the versatile catalyst system Na2[PdCl4]/PR3/CuI (PR3=(1-Ad)2PBn, PtBu3), the Sonogashira coupling [Eq. (a)] of aryl chlorides with alkynes generates excellent yields of the corresponding disubstituted aryl alkynes.Keywords:
Sonogashira coupling
Aryl chlorides are suitable substrates for the Sonogashira coupling! By using the versatile catalyst system Na2[PdCl4]/PR3/CuI (PR3=(1-Ad)2PBn, PtBu3), the Sonogashira coupling [Eq. (a)] of aryl chlorides with alkynes generates excellent yields of the corresponding disubstituted aryl alkynes.
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Terminal alkynes react with aryl bromides in water at ambient temperature in the presence of an amphiphilic nanomicelle-forming reagent PTS. The development of new processes using pure water as a solvent is quite important for the chemical industry, since they allow decreasing the amount of the produced wastes as well as the manufacturing costs of products.
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Indazole
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An efficient and general protocol for the deacetonative Sonogashira coupling of aryl propargyl alcohols with aryl chlorides is described. The reaction proceeded smoothly with the catalyst system of palladacycle/Xphos. This result represents the first successful deacetonative Sonogashira version for electron-poor, electron-neutral, and even inactive sterically hindered electron-rich aryl chlorides.
Sonogashira coupling
Propargyl
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Synthesis of a 2-Aminoimidazole Library for Antibiofilm Screening Utilizing the Sonogashira Reaction
The divergent synthesis of a 21-member library composed of 2-aminoimidazole compounds for evaluation as novel antibiofilm molecules is presented. The Sonogashira reaction was employed with three regioisomeric aryl iodides and 11 different alkynes to generate variously substituted diverse ring systems. Good to excellent yields (80−97%) for the reaction were obtained, and the products provide adequate handles for further manipulation into more advanced analogues.
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The Sonogashira reaction of aryl chlorides is a challenging process with only limited success that has so far been achieved. The present method describes a fast (in minutes) and convenient microwave-assisted coupling of aryl chlorides, including electron-rich substrates, such as terminal alkynes, which can be especially useful for the synthesis of compounds libraries. Alkenyl chlorides are also suitable substrates under the described reaction conditions.
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Sonogashira coupling
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Sonogashira coupling
Coupling reaction
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Hitherto unknown pentaalkynylpyridines have been prepared in high yields by Sonogashira cross-coupling reactions of pentachloropyridine. Their photophysical properties were studied and compared to those of penta- and hexaalkynylbenzenes which were efficiently prepared by the first Sonogashira reactions of pentachlorobenzene and hexachlorobenzene. The pentaalkynylpyridines show promising fluorescence properties because of their high quantum yields.
Sonogashira coupling
Hexachlorobenzene
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