The first stereospecific arylation of (<i>Z</i>)‐germyl(stannyl)ethenes with an aryl halide or heteroaryl halide under palladium‐catalysis

On the basis of the strategy of developing highly efficient protocol for Pd-catalyzed cross-coupling reactions, a series of bulky bis(imino)acenaphthene (BIAN)-supported Pd-PEPPSI complexes were synthesized, characterized, and applied in direct arylation of azoles. The effect of backbone and N-moieties on NHCs was evaluated, and the reaction conditions were optimized. It was found that the bulky Pd-PEPPSI complexes could be successfully employed in cross-coupling of (hetero)aryl bromides with azoles at a low palladium loading of 0.5–0.05 mol % under aerobic conditions, demonstrating the ease of manipulation without glovebox and handling of solvents.

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Fluoride-Promoted Cross-Coupling of Chloro(mono-, di-, or triphenyl)germanes with Aryl Halides in “Moist” Toluene. Multiple Transfer of the Phenyl Group from Organogermane Substrates and Comparison of the Coupling Efficiencies of Chloro(phenyl)germanes with their Corresponding Stannane and Silane Counterparts

Pitteloud

Zhang

Liang

et al. 2010

J. Org. Chem.

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The trichlorophenyl-, dichlorodiphenyl-, and chlorotriphenylgermanes undergo Pd-catalyzed cross-couplings with aryl bromides and iodides in the presence of tetrabutylammonium fluoride in toluene with addition of the measured amount of water. One chloride ligand on the Ge center allows efficient activation by fluoride to promote transfer of one, two or three phenyl groups from the organogermanes. The corresponding chlorophenylstannanes were found to be more reactive than chlorophenylsilanes, which in turn were more effective than chlorophenylgermanes. One chloride ligand on Ge or Si center allows efficient activation by fluoride to promote transfer of up to three aryl groups from germane or silicon. However, no haloligand was necessary to be present on Sn center, since tetraphenyltin efficiently transferred up to four phenyl groups during fluoride-promoted couplings with aryl halides. 19F NMR studies suggested formation of the fluorophenylgermanes and the hypervalent germanate species as possible intermediates.

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The first stereospecific arylation of (Z)‐germyl(stannyl)ethenes with an aryl halide or heteroaryl halide under palladium‐catalysis

Cited by 3 publications

References 17 publications

ChemInform Abstract: The First Stereospecific Arylation of (Z)‐Germyl(stannyl)ethenes with an Aryl Halide or Heteroaryl Halide under Palladium‐Catalysis.

ChemInform Abstract: The First Stereospecific Arylation of (Z)‐Germyl(stannyl)ethenes with an Aryl Halide or Heteroaryl Halide under Palladium‐Catalysis.

Developing Bis(imino)acenaphthene-Supported N-Heterocyclic Carbene Palladium Precatalysts for Direct Arylation of Azoles

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