Completion of a catalytic cycle of zirconium-catalyzed alkylation of silanes by addition of organic halides

Ura, Yasuyuki; Hara, Ryuichiro; Takahashi, Tamotsu

doi:10.1039/b002516j

Cited by 5 publications

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“…In addition, observation of a small amount of styrene in the reaction mixture suggests that the phenethylmagnesium group isomerizes to a secondary one via styrene on the catalyst. 2c,, To clarify this phenomenon, reactions of 2-phenethylmagnesium chloride with TaCl 5 without aryl halides followed by quenching with NCS were performed as shown in Scheme . The reaction with 100 mol % TaCl 5 afforded the isomerized product (1-chloroethyl)benzene ( 2 ) in 90% as a sole product.…”

Section: Resultsmentioning

confidence: 99%

Early Transition Metal-Catalyzed Cross-Coupling Reaction of Aryl Fluorides with a Phenethyl Grignard Reagent Accompanied by Rearrangement of the Phenethyl Group

et al. 2006

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Defluorination of 1-fluoronaphthalene was catalyzed by CpTiCl3 and an alkyl Grignard reagent system. The reaction of 1-fluoronaphthalene, however, with 3 equiv of phenethylmagnesium chloride in the presence of a catalytic amount of transition metal catalysts afforded 1-(1-phenethyl)naphthalene in good yield via isomerization of the phenethyl group. Among the examined catalysts, CpTiCl3 and TaCl5 showed much higher activity than the others. The similar coupling reactions of phenethylmagnesium chloride with substituted fluoroarenes proceeded with high regioselectivity at the para-position to produce the corresponding 1-phenethylarenes in good yields.

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