An acetatopalladium(II) complex with 1‐benzyl‐N‐(3,5‐di‐tert‐butylsalicylidene)piperidin‐4‐amine: Synthesis, structure and catalytic applications in Suzuki–Miyaura coupling of arylboronic acids with hydroxyaryl halides

doi:10.1002/AOC.3778

Paper

An acetatopalladium(II) complex with 1‐benzyl‐N‐(3,5‐di‐tert‐butylsalicylidene)piperidin‐4‐amine: Synthesis, structure and catalytic applications in Suzuki–Miyaura coupling of arylboronic acids with hydroxyaryl halides

Published Nov 1, 2017 · Srinivas Keesara, G. N. Babu, S. Pal

Applied Organometallic Chemistry

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Abstract

The Schiff base 1-benzyl-N-(3,5-di-tert-butylsalicylidene)piperidin-4-amine (HL) and its acetatopalladium(II) complex having the formula [Pd(L)(OAc)] were synthesized. Both HL and [Pd(L)(OAc)] were characterized using elemental analysis and various spectroscopic (infrared, UV–visible, 1H NMR and 13C NMR) and mass spectrometric measurements. The molecular structure of the complex was determined using X-ray crystallographic analysis. In the complex, the pincer-like NNO-donor L− and the monodenate OAc− provide a distorted square-planar N2O2 coordination environment around the metal centre. The physicochemical properties and the spectroscopic features of [Pd(L)(OAc)] are consistent with its molecular structure. The complex was found to be an effective catalyst for the Suzuki–Miyaura cross-coupling reactions of hydroxyaryl halides with arylboronic acids in predominantly aqueous media. The reactions afforded hydroxybiaryl products in good to excellent yields with a wide substrate scope.

Study Snapshot

The acetatopalladium(II) complex with 1-benzyl-N-(3,5-di-tert-butylsalicylidene)piperidin-4-amine effectively catalyzes the Suzuki-Miyaura cross-coupling reaction of hydroxy

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

An acetatopalladium(II) complex with 1‐benzyl‐N‐(3,5‐di‐tert‐butylsalicylidene)piperidin‐4‐amine: Synthesis, structure and catalytic applications in Suzuki–Miyaura coupling of arylboronic acids with hydroxyaryl halides

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Citations

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Acetonitrile-bridged dinuclear palladium complex 1 and organopalladium complex 1' were synthesized selectively using acetonitrile and ethanol, with the first example showing an exceptionally short C-N bond distance.

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A new approach for carbon-carbon bond formation in water using Pd(OAc)2(PPh_3)_2 supported on magnesium hydroxide and cerium carbonate hydroxide catalyst allows for mild conditions and smooth transformation of aryl halides into biaryls.

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