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

Alicia Castelló-Micó; Julia Nafe; Kosuke Higashida; Konstantin Karaghiosoff; Marc Gingras; Paul Knochel

doi:10.1021/acs.orglett.6b03539

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

Org Lett. 2017 Jan 20;19(2):360-363. doi: 10.1021/acs.orglett.6b03539. Epub 2016 Dec 30.

Authors

Alicia Castelló-Micó¹, Julia Nafe¹, Kosuke Higashida¹, Konstantin Karaghiosoff¹, Marc Gingras², Paul Knochel¹

Affiliations

¹ Department Chemie, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 München, Germany.
² CNRS, Aix-Marseille Université, CINAM UMR 7325 , 163 Avenue de Luminy, 13288 Marseille, France.

PMID: 28035825
DOI: 10.1021/acs.orglett.6b03539

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't