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Non-ortho-substituted aryl iodides gave inferior results. When ethyl 4-iodobenzoate was subjected to the reaction conditions, the desired product was obtained in 34% yield. See the Supporting Information.
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34
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84926164792
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note
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The best results were obtained when 1 equiv of norbornene was employed. When 25 mol % was used, the desired products were obtained in lower yields. See the Supporting Information.
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35
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84926198757
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Additionally, cyanation (ref 6a) and N -tosylhydrazone insertion (refs 7d, 7e, and 7f) have also been employed.
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Aminoboronate 2t was resubjected to the reaction conditions in the presence of benzoic acid. 1H NMR analysis of the reaction mixture revealed no generation of the corresponding ipso -hydrogenation product.
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43
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Dong and co-workers have hypothesized that under the reaction conditions, the imine or enamine generated upon elimination of benzoate from N -benzoyloxyamines may serve as the reductant. See ref 9.
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