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Metallation of N-vinylpyrroles and -indoles with Hg(OAc)2: N-vinyl vs. pyrrole nucleophilic sites
Authors:Trofimov Boris A  Ivanov Andrey V  Ushakov Igor A  Schmidt Elena Yu  Sobenina Lyubov N  Vasil'tsov Alexander M  Mikhaleva Albina I
Institution:A E Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation. boris_trofimov@irioch.irk.ru
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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