Palladium(II) complexes containing sterically bulky O, N donor ligands: Synthesis, characterization and catalytic activity in the Suzuki-Miyaura and Sonogashira coupling reactions

Nandhini, R.; Vijayan, Paranthaman; Venkatachalam, Galmari

doi:10.1016/j.jorganchem.2019.121080

Cited by 6 publications

(1 citation statement)

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“…Interestingly, several nitrogenated ligands have been also employed for the Suzuki-Miyaura cross-coupling. We can quote for example the use of Schiff bases [44][45][46][47][48][49][50], amines [51,52], azo compounds [53], pyridines [54][55][56][57][58], pyrimidines [59,60], triazoles [61] or benzimidazoles [62]. However, despite their relevance, these catalytic systems suffer from one or more drawbacks such as the use of expensive or difficultly accessible ligands, as well as high catalyst loading, hazardous solvents and harsh reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed Suzuki–Miyaura cross-coupling with α-aminophosphonates based on 1,3,4-oxadiazole as ligands

Hkiri¹,

Touil²,

Samarat³

et al. 2022

Comptes Rendus. Chimie

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The synthesis of a palladium complex bearing two diethyl[(5-phenyl-1,3,4-oxadiazol-2ylamino)(4-nitrophenyl)methyl]phosphonates as ligands has demonstrated the ability of this type of α-aminophosphonates to coordinate to the palladium(II) ion via their electronically enriched nitrogen atom of the 1,3,4-oxadiazole ring. The complex was fully characterized by elemental analysis, infrared, NMR and mass spectrometry. A solid-state structure revealed the trans coordination of the two nitrogenated ligands. The presence of a hemilabile P(O)(OEt) 2 moiety in the α-aminophosphonates was exploited into palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl halides. The formation of (N ,O)-chelate intermediates may increase the steric hindrance and the electronic density of the metal, which should favor the oxidative addition and the reductive elimination/product decoordination elementary steps. With our catalytic systems, good activities for the formation of orthodi/trisubstituted biphenyl compounds were observed from aryl bromides using only 0.5 mol% of palladium. Cross-coupling of aryl chlorides required a catalyst loading of 1 mol% to generate orthosubstituted biphenyls.

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