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Selective Multiple Magnesiations of the Thieno[3,2-b]thiophene Scaffold

Authors

  • M. Sc. Thomas Kunz,

    1. Department Chemie, Ludwig-Maximilians-Universtät München, Butenandtstrasse 5–13, 81377 München (Germany), Fax: (+49) 89-2180-77680
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  • Prof. Dr. Paul Knochel

    Corresponding author
    1. Department Chemie, Ludwig-Maximilians-Universtät München, Butenandtstrasse 5–13, 81377 München (Germany), Fax: (+49) 89-2180-77680
    • Department Chemie, Ludwig-Maximilians-Universtät München, Butenandtstrasse 5–13, 81377 München (Germany), Fax: (+49) 89-2180-77680
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Abstract

A full functionalization of all four positions of the thieno[3,2-b]thiophene scaffold was achieved. Starting from 2,5-dichlorothieno[3,2-b]thiophene, magnesiation of the 3- and 6-position using tmpMgCl⋅LiCl furnishes, after trapping with various electrophiles, 3,6-difunctionalized dichlorothieno[3,2-b]thiophenes. Subsequent dechlorination and regioselective metalation or regioselective magnesium insertion into the C[BOND]Cl bond provides fully functionalized thieno[3,2-b]thiophenes. Furthermore, new condensed heterocycles and small oligomers of these compounds with potential applications in material chemistry have been prepared.

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