ChemInform Abstract: Palladium‐Catalyzed Cross‐Coupling Reaction of Terminal Alkynes with 2‐ Trialkylsilyl(germyl)‐1‐haloalkenylalkyl Esters. Synthesis of Element‐ Substituted 2‐Alkoxy‐1,3‐enynes.

Efimova, I. V.; Golyavin, A. A.; Kazankova, M. A.; Beletskaya, I. P.

doi:10.1002/chin.199602046

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“…Although systems which will allow direct comparison of the cross-coupling reactions between the organometallic reagents derived from group 14 metals and electrophiles are lacking, − organochlorogermanes can render a coupling efficiency comparable to the usually more reactive stannane and silane counterparts. , Therefore, herein, we report a comparative study on the reactivity of chlorophenylgermanes and their corresponding silanes and stannanes counterparts toward TBAF-promoted Pd-catalyzed cross-couplings with aryl halides in wet toluene, as well as some mechanistic considerations.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2010

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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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