4-(3,5-Dimethylphenyl)benzyl alcohol synthesis

Yield:885963-96-2 98 %Spectr.

Reaction Conditions:

with C₄₇H₆₂N₄O₄PdS₂;potassium carbonate in water at 60; for 0.166667 h;Green chemistry;Suzuki-Miyaura Coupling;

Steps:

Catalysis Experiments

General procedure: In a typical in situ catalyst generation approach for the C-C coupling reaction, (4-bromophenyl)methanol (0.19 g, 1.0 mmol), phenylboronic acid (0.46 g, 1.2 mmol), K₂CO₃ (0.14 g, 1.0 mmol), Pd(OAc)₂ (0.2 mol-% relative to the aryl bromide), and a given ligand (0.4 mol-%) were weighed into a 10 mL round-bottom flask equipped with a magnetic stirrer and reacted in water (4 mL) for a given reaction duration. In the case of a preformed palladium(II) complex, 0.2 mol-% equivalent relative to the aryl bromide was used in place of the ‘Pd(OAc)₂+ligand’ deployed for the in situ complex generation. After the reaction, an aliquot of the reaction mixture was transferred into a clean conical flask and the solvent was removed under vacuum. The residue was collected in deuterated DMSO and its ¹H NMR spectrum analysed. The yields were evaluated by comparing integration values for the NMR signal for the methylene CH₂ protons of (4-bromophenyl)methanol at ~4.4 ppm against the CH₂ function of the resulting biphenyl products at ~4.7 ppm (see Fig. S1 in the Supplementary Material for illustration).^[59,60] The biphenyl products have been characterised in our previous studies.^[19,59,61]

References:

Oloyede, Hammed Olawale;Akong Akong, Raymond;Woods, Joseph Anthony Orighomisan;G?rls, Helmar;Plass, Winfried;Eseola, Abiodun Omokehinde [Australian Journal of Chemistry,2021,vol. 74,# 2,p. 101 - 110]