Aromatic allylation via diazotization: metal-free C-C bond formation |
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Authors: | Ek Fredrik Axelsson Oskar Wistrand Lars-Göran Frejd Torbjörn |
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Affiliation: | Organic Chemistry 1, Department of Chemistry, Lund University, P.O. Box 124, S-221 00 Lund, Sweden. |
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Abstract: | A new method for the synthesis of allyl aromatic compounds not involving any metal-containing reagent or catalyst has been developed. Arylamines substituted with a large number of different substituents were converted via diazotizative deamination with tert-butyl nitrite in allyl bromide and acetonitrile to the corresponding allyl aromatic compounds. The allylation reaction was found to be suitable for larger scale synthesis due to short reaction times, a nonextractive workup, and robustness toward moisture, air, and type of solvent. |
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