Cu(II) Catalyzed Imine C–H Functionalization Leading to Synthesis of 2,5-Substituted 1,3,4-Oxadiazoles

• Published in: Organic letters Vol. 13; no. 22; pp. 5976 - 5979
• Main Authors: Guin, Srimanta, Ghosh, Tuhin, Rout, Saroj Kumar, Banerjee, Arghya, Patel, Bhisma K
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 18.11.2011; Amer Chemical Soc
• Subjects: Carbon - chemistry; Catalysis; Chemistry; Chemistry, Organic; Copper - chemistry; Hydrogen - chemistry; Imines - chemistry; Molecular Structure; Oxadiazoles - chemical synthesis; Oxidation-Reduction; Physical Sciences; Science & Technology; LIGHT-EMITTING-DIODES; DIRECT ARYLATION; DIRECT AMINATION; ONE-POT SYNTHESIS; 2-ARYLBENZOXAZOLES; BENZODIAZEPINE; BENZOXAZOLES; N BOND FORMATION; OPTIMIZATION; OXADIAZOLES

A direct access to symmetrical and unsymmetrical 2,5-disubstituted [1,3,4]-oxadiazoles has been accomplished through an imine C–H functionalization of N-arylidenearoylhydrazide using a catalytic quantity of Cu(OTf)2. This is the first example of amidic oxygen functioning as a nucleophile in a Cu-cat...