Reactivity of mixed organozinc and mixed organocopper reagents: 14. Phosphine-nickel catalyzed aryl-allyl coupling of (n-butyl)(aryl)zincs. Ligand and substrate control on the group selectivity and regioselectivity

Kalkan, Melike; Erdık, Ender

doi:10.1016/j.jorganchem.2016.05.014

Cited by 4 publications

(2 citation statements)

References 56 publications

(20 reference statements)

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“…As ligands, we chose monodentate phosphine ligands, L = Ph 3 P, ( c -Hexyl) 3 P and a bidentate phosphine ligand, L = dppf (1,2-bisdiphenylphosphino ferrocene), which we recently found as active ligands in the NiCl 2 .L 2 catalyzed aryl-allyl coupling of (n -butyl)(aryl)zincs. 69 We also investigated the catalytic activity of nano-NiO in the acylation reaction. For this purpose, we chose nano-NiO ( <50 nm) as the first example.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of some ketones via nano-nickel oxide catalyzed acylation of arylzinc reagents; strategy involving the use of mixed (methyl)(aryl)zincs

2018

Turk J Chem

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Nano-NiO catalyzed acylation of mixed (methyl)(aryl)zincs with aromatic acyl halides in THF at room temperature provides a new facile route for aryl-aroyl coupling. Among NiCl 2 .L 2 and NiCl 2 .L (L = monodentate and bidentate phosphine ligand) catalysts, the lower catalyst loading of NiCl 2 (dppf) may seem attractive; however, nano-NiO, being the lowest cost catalyst, is more favorable for aroylation of (methyl)(aryl)zincs. This procedure also provides a supplement to Cu and Pd catalyzed acylation of diorganozincs.

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Section: Resultsmentioning

confidence: 99%

Synthesis of some ketones via nano-nickel oxide catalyzed acylation of arylzinc reagents; strategy involving the use of mixed (methyl)(aryl)zincs

2018

Turk J Chem

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“…GC analyses were performed on a Thermo Phenylmagnesium bromide was prepared in THF according to standard procedure and its concentration was found by titration prior to use (41). For authentic samples, 1-phenyl-2-butene was purchased and 3-phenyl-1-butene was synthesized (42). Yields and product ratios are given as average of at least two experiments.…”

Section: Methodsmentioning

confidence: 99%

Allylation of Aryl Grignard Reagents in the Presence of Transition Metal Catalysis and Organic Catalysis

Kalkan¹

2017

Journal of the Turkish Chemical Society, Section A: Chemistry

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The allylation yield and regioselectivity of phenyl Grignard reagent in THF was investigated in the presence of complexed transition metals and also uncomplexed or complexed transition metal salts. Additionally, the effect of Lewis acids and Lewis bases on the yield and the regioselectivity of the allylic arylation was also observed. Neither P-containing ligands for transition metal complexes, nor transition metal salts did make a difference on the yield and : product ratio and gave the is -product as the main product. However, donor cosolvents resulted in decrease in the yield and change of the regioselectivity.

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Catalytic prenylation and reverse prenylation of aromatics

Min

2022

Trends in Chemistry

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Reactivity of mixed organozinc and mixed organocopper reagents: 14. Phosphine-nickel catalyzed aryl-allyl coupling of (n-butyl)(aryl)zincs. Ligand and substrate control on the group selectivity and regioselectivity

Cited by 4 publications

References 56 publications

Synthesis of some ketones via nano-nickel oxide catalyzed acylation of arylzinc reagents; strategy involving the use of mixed (methyl)(aryl)zincs

Synthesis of some ketones via nano-nickel oxide catalyzed acylation of arylzinc reagents; strategy involving the use of mixed (methyl)(aryl)zincs

Allylation of Aryl Grignard Reagents in the Presence of Transition Metal Catalysis and Organic Catalysis

Catalytic prenylation and reverse prenylation of aromatics

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