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

Kuno Schwärzer | Zendy; Carl Phillip Tüllmann | Zendy; Simon Graßl | Zendy; Bartosz Górski | Zendy; Cara E. Brocklehurst | Zendy; Paul Knochel | Zendy

Open Access

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

Author(s) -

Kuno Schwärzer,

Carl Phillip Tüllmann,

Simon Graßl,

Bartosz Górski,

Cara E. Brocklehurst,

Paul Knochel

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c00238

Subject(s) - chemistry , electrophile , regioselectivity , metalation , surface modification , combinatorial chemistry , benzoates , organic chemistry , catalysis

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) TMP 2 Zn·2LiCl, TMP 2 Zn·2MgCl 2 ·2LiCl, TMPMgCl·LiCl, and TMPZnCl·LiCl under mild conditions in THF. Subsequent trapping with various electrophiles including hydroxylamino benzoates gives access to functionalized heterocycles while tolerating many functional groups.

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