Selective multiple magnesiations of the thieno[3,2-b]thiophene scaffold |
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Authors: | Kunz Thomas Knochel Paul |
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Affiliation: | Department Chemie, Ludwig‐Maximilians‐Universt?t 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? 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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Keywords: | C?H activation cross‐coupling magnesium metalation regioselectivity |
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