Palladium-catalysed reactions of aryl halides with soft, non-organometallic nucleophiles
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Aryl halide
Based on DFT calculations, a new mechanism for the oxidative addition of aryl halides to Pd-catalysts is presented. The key intermediate is an anionic Pd-species in which the aryl halide coordinates to the palladium via the halide atom.
Oxidative addition
Aryl halide
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Herein, an efficient and general protocol for the cyanomethylation of aryl halides and triflates is disclosed. A wide range of electron-donating or electron-accepting functional groups is tolerated on the aryl halide and the desired products are obtained in good yields.
Aryl halide
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We report here the rapid halide exchange in aryl halides facilitated by microwave and conventional heating using nickel(II) halides as reagents. The methodology can be used for conversion of aryl chlorides to bromides, aryl iodides to bromides and chlorides and aryl bromides to chlorides. Reactions are fast (5 minutes reaction time for microwave heating and 4 hours for conventional heating) and can be performed without the need for exclusion of air and water.
Microwave heating
Aryl halide
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Corrected by: Coupling of Aryl Halides and Diaryl Diselenides with CuS/FeSynfacts 2011; 2011(03): 0348-0348DOI: 10.1055/s-0030-1259577
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Abstract A simple and convenient one‐pot synthesis of aryl alkyl ethers by the alkoxylation of aryl halides in the presence of Triton B as nonmetallic base is described.
Base (topology)
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Organometallic Chemistry
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The relative rates of nucleophilic displacement by halide ions from tetra-n-pentylammonium cations in the molten tetrapentylammonium salts at 180°(Cl–:Br–:I–= 620:7·7:1) reflect the enhanced nucleophilicity expected for unsolvated, unassociated halide ions.
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Abstract A palladium‐catalyzed direct C‐arylation reaction of readily available cage carboranyllithium reagents with aryl halides has been developed for the first time. This method is applicable to a wide range of aryl halide substrates including aryl iodides, aryl bromides, and heteroaromatic halides.
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Correction to: Coupling of Aryl Halides and Diaryl Diselenides with CuS/FeSynfacts 2011; 2011(01): 0106-0106DOI: 10.1055/s-0030-1259133
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The first example of visible-light-driven reductive carboarylation of styrenes with CO2 and aryl halides in a regioselective manner has been achieved. A broad range of aryl iodides and bromides were compatible with this reaction. Moreover, pyridyl halides, alkyl halides, and even aryl chlorides were also viable with this method. These findings may stimulate the exploration of novel visible-light-driven Meerwein arylation-addition reactions with user-friendly aryl halides as the radical sources and the photocatalytic utilization of CO2.
Visible spectrum
Aryl halide
Aryl radical
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