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Castelló-Micó, Alicia; Nafe, Julia; Higashida, Kosuke; Karaghiosoff, Konstantin; Gingras, Marc; Knochel, Paul (2017): Selective Metalations of 1,4-Dithiins and Condensed Analogues Using TMP-Magnesium and -Zinc Bases. In: Organic Letters, Vol. 19, No. 2: pp. 360-363
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Abstract

TMPMgCl center dot LiCl and TMPZnCl center dot 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.