Pd(OAc)2/DABCO as an Inexpensive and Efficient Catalytic System for Hiyama Cross-Coupling Reactions of Aryl Halides with Aryltrimethoxysilanes
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Abstract:
Pd(OAc)2/DABCO was found to be an inexpensive and efficient catalyst system for Hiyama cross-coupling reactions of aryl halides with aryltrimethoxysilanes. In the presence of Pd(OAc)2, DABCO, and TBAF, coupling of a number of aryl halides with aryltrimethoxysilanes underwent efficiently to afford the corresponding cross-coupled products in moderate to excellent yields.Keywords:
DABCO
Coupling reaction
Aryl halide
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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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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Aryl and benzylic zinc bromides undergo efficient Pd(0)-catalyzed cross-coupling reactions on the solid-phase using either Rink or Wang resin. By performing the cross-couplings with the multi-coupling reagents 2 and 3 two successive carbon-carbon bond forming reactions are possible on the solid-phase.
Coupling reaction
Solid-Phase Synthesis
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Substoichiometric amounts of ZnCl2 promote the room temperature, Pd/P(t-Bu)3-catalyzed cross-coupling of aryl bromides with alkynes. Pd(I) dimer 1 is demonstrated to be a particularly active precatalyst for this reaction. The reaction is general for a wide variety of aryl bromides.
Alkyne
Coupling reaction
Zinc bromide
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An extended study of the reactivity of potassium aryl- and heteroaryltrifluoroborates in Suzuki-Miyaura cross-coupling reactions is presented. The coupling of aryl- and electron-rich heteroaryltrifluoroborates with aryl and activated heteroaryl bromides proceeds readily under ligandless conditions. When deactivated aryl- and heteroaryltrifluoroborates are coupled with aryl and heteroaryl bromides and chlorides, a low loading (0.5-2%) of PdCl(2)(dppf).CH(2)Cl(2) efficiently catalyzes the reactions. Under either condition, reactions can generally be carried out in an open atmosphere.
Coupling reaction
Reactivity
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An investigation into Pd-catalyzed C−N cross-coupling reactions of aryl iodides is described. NaI is shown to have a significant inhibitory effect on these processes. By switching to a solvent system in which the iodide byproduct was insoluble, reactions of aryl iodides were accomplished with the same efficiencies as aryl chlorides and bromides. Using catalyst systems based on certain biarylphosphine ligands, aryl iodides were successfully reacted with an array of primary and secondary amines in high yields. Lastly, reactions of heteroarylamines and heteroaryliodides were also conducted in high yields.
Coupling reaction
Primary (astronomy)
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Abstract The sections in this article are Introduction Anodic Processes Halogenated Alkanes Alicyclic Halides Aryl Halides Cathodic Processes Halogenated Alkanes Halogenated Alkenes and Alkynes Benzyl Halides Alicyclic Halides Aryl Halides Acyl and Phenacyl Halides Aliphatic α‐Halocarbonyl Compounds Halogenated Heterocyclic Compounds Catalytic Reduction of Carbon–Halogen Bonds
Alicyclic compound
Phenacyl
Aryl halide
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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.
Aryl halide
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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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