Electrochemical Intramolecular CH Amination: Synthesis of Benzoxazoles and Benzothiazoles

• Published in: Chemistry : a European journal Vol. 21; no. 8; pp. 3211 - 3214
• Main Authors: Morofuji, Tatsuya, Shimizu, Akihiro, Yoshida, Jun-ichi
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 16.02.2015; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Amination; Aminobenzothiazoles; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; CH amination; CH functionalization; Electrochemical oxidation; Electrochemistry; Oxidation; Phenols; Physical Sciences; Piperidine; radical ions; Science & Technology; Synthesis; Thiophenol; HALIDES; C-H amination; BENZAZOLES; electrochemistry; radical ions; CATALYZED SYNTHESIS; ARENES; oxidation; 2-ARYLBENZOXAZOLES; C-H functionalization; N BOND FORMATION; 2-SUBSTITUTED BENZOTHIAZOLES; INHIBITORS; DERIVATIVES; ANODIC-OXIDATION; CH amination; CH functionalization
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201406398

A new method for metal‐free intramolecular CH amination has been developed. Electrochemical oxidation of 2‐pyrimidyloxybenzenes and 2‐pyrimidylthiobenzenes, which can be easily prepared from phenols and thiophenols, respectively, followed by the treatment of the resulting pyrimidinium ions with piperidine gives 2‐aminobenzoxazoles and 2‐aminobenzothiazoles, respectively. Integration of electrochemical and chemical reactions: A new method for metal‐free intramolecular CH amination has been developed. Electrochemical oxidation of 2‐pyrimidyloxybenzenes and 2‐pyrimidylthiobenzenes, which can be easily prepared from phenols and thiophenols, respectively, followed by the treatment of the resulting pyrimidinium ions with piperidine gives 2‐aminobenzoxazoles and 2‐aminobenzothiazoles, respectively.