Kinetics and mechanism of nickel reaction with benzyl bromide in dimethylformamide

Егоров, А.М.; Matyukhova, S. A.; Kocherova, I. S.; Novikova, A. A.; Анисимов, А. В.

doi:10.1134/s1070363209030177

Cited by 4 publications

(1 citation statement)

References 18 publications

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“…1-Bromoethyl Benzene (11m). 65 The following reagents were combined in the amounts and method indicated according to general procedure 3. 1-Phenylethyl alcohol (122 mg, 1.00 mmol, oxalyl chloride (110 μL, 1.30 mmol), LiBr (217 mg, 2.50 mmol), triphenylphosphine oxide (42 mg, 0.15 mmol).…”

Section: Synthesis Of Bromidesmentioning

confidence: 99%

Catalytic Phosphorus(V)-Mediated Nucleophilic Substitution Reactions: Development of a Catalytic Appel Reaction

et al. 2011

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Catalytic phosphorus(V)-mediated chlorination and bromination reactions of alcohols have been developed. The new reactions constitute a catalytic version of the classical Appel halogenation reaction. In these new reactions oxalyl chloride is used as a consumable stoichiometric reagent to generate the halophosphonium salts responsible for halogenation from catalytic phosphine oxides. Thus, phosphine oxides have been transformed from stoichiometric waste products into catalysts and a new concept for catalytic phosphorus-based activation and nucleophilic substitution of alcohols has been validated. The present study has focused on a full exploration of the scope and limitations of phosphine oxide catalyzed chlorination reactions as well as the development of the analogous bromination reactions. Further mechanistic studies, including density functional theory calculations on proposed intermediates of the catalytic cycle, are consistent with a catalytic cycle involving halo- and alkoxyphosphonium salts as intermediates.

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Section: Synthesis Of Bromidesmentioning

confidence: 99%