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Selective Metalations of 1,4-Dithiins and Condensed Analogues Using TMP-Magnesium and -Zinc Bases

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journal contribution
posted on 30.12.2016, 15:21 by Alicia Castelló-Micó, Julia Nafe, Kosuke Higashida, Konstantin Karaghiosoff, Marc Gingras, Paul Knochel
TMPMgCl·LiCl and TMPZnCl·LiCl allow facile magnesiation and zincation, respectively, of the 1,4-dithiin scaffold, producing polyfunctionalized 1,4-dithiins. A subsequent metalation of these S-heterocycles can also be achieved with the same TMP bases, leading to 2,3-disubstituted-1,4-dithiins. The Mg- and Zn-TMP bases allow as well the successful metalation of 1,4,5,8-tetrathianaphthalene and 1,4,5,6,9,10-hexathiaanthracene.