Metallation of N-vinylpyrroles and -indoles with Hg(OAc)2: N-vinyl vs. pyrrole nucleophilic sites |
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Authors: | Trofimov Boris A Ivanov Andrey V Ushakov Igor A Schmidt Elena Yu Sobenina Lyubov N Vasil'tsov Alexander M Mikhaleva Albina I |
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Institution: | A E Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation. boris_trofimov@irioch.irk.ru |
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Abstract: | N-Vinylpyrroles and -indoles bearing electron-withdrawing substituents at the pyrrole ring are mercurated, with 1 equivalent of Hg(OAc)(2) in dry MeCN (20-80 °C), regioselectively at the vinyl group (yields are almost quantitative), while their congeners without electron-withdrawing functions are mercurated both at the N-vinyl group and the pyrrole ring. |
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