Functionalization of 1,3,4-Oxadiazoles and 1,2,4-Triazoles via Selective Zincation or Magnesiation Using 2,2,6,6-Tetramethylpiperidyl Bases

Schwarzer, Kuno; Tullmann, Carl Phillip; Grassl, Simon; Gorski, Bartosz; Brocklehurst, Cara E. und Knochel, Paul (2020): Functionalization of 1,3,4-Oxadiazoles and 1,2,4-Triazoles via Selective Zincation or Magnesiation Using 2,2,6,6-Tetramethylpiperidyl Bases. In: Organic Letters, Bd. 22, Nr. 5: S. 1899-1902

Abstract

We report the metalation of the 1,3,4-oxadiazole and 1,2,4-triazole scaffolds via regioselective zincation or magnesiation using the TMP bases (TMP = 2,2,6,6-tetramethylpiperidyl) TMP2Zn center dot 2LiCl, TMP2Zn center dot 2MgCl(2)center dot 2LiCl, TMPMgCl center dot LiCl, and TMPZnCl center dot LiCl under mild conditions in THF. Subsequent trapping with various electrophiles including hydroxylamino benzoates gives access to functionalized heterocycles while tolerating many functional groups.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1523-7060
• Sprache: Englisch