Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 22, Pages 11184-11193Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo401445j
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Funding
- CSIR, India [08/003(0072)/2010-EMR-I, 08/003(0083)/2011-EMR-1]
- CSIR-India [01(2459)/11/EMR-II]
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s-Tetrazine based molecules were prepared for visible-light-driven organic transformations. The 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) derivative shows visible light absorption and reversible one-electron reduction behavior. In the presence of pytz and aerial oxygen, aldehyde reacts with o-phenylenediamine or o-aminothiophenol under visible light irradiation at ambient temperature to produce corresponding 2-substituted benzimidazoles and benzothiazoles, respectively. Pytz catalyst demonstrates excellent catalytic activity for alkyl, aryl, organo-metallic substituted aldehydes and reducing sugar. The reaction yield is high for both the electron-donating and electron withdrawing substituents in aromatic aldehydes. The use of a metal-free catalyst and visible light energy, along with the mild reaction conditions, makes this reaction an environmentally benign and energy-saving chemical process.
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