Mo‐Based Oxidizers as Powerful Tools for the Synthesis of Thia‐ and Selenaheterocycles

A highly efficient synthetic protocol for the synthesis of thia‐ and selenaheterocycles has been developed. By employing a MoCl5‐mediated intramolecular dehydrogenative coupling reaction, a broad variety of structural motifs was isolated in yields up to 94 %. The electrophilic key transformation is...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-02, Vol.25 (8), p.1936-1940
Main Authors: Franzmann, Peter, Beil, Sebastian B., Schollmeyer, Dieter, Waldvogel, Siegfried R.
Format: Article
Language:English
Subjects:
Atom economy
Chemistry
cyclization
C−H activation
Dehydrogenation
Halides
molybdenum
oxidation
Oxidizing agents
sulfur heterocycles
Synthesis
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Summary:A highly efficient synthetic protocol for the synthesis of thia‐ and selenaheterocycles has been developed. By employing a MoCl5‐mediated intramolecular dehydrogenative coupling reaction, a broad variety of structural motifs was isolated in yields up to 94 %. The electrophilic key transformation is tolerated by several labile moieties like halides and tertiary alkyl groups. Due to the use of disulfide or diselenide precursors, a high atom efficiency was achieved. Molybdenum opens the door as pentachloride or as an anode material to synthesize a variety of thia‐ and selenaheterocycles in high yields up to 94 %. The dehydrogenative coupling of disulfides and diselenides leads to an excellent atom economy for the key transformation.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201805938