Synthesis of cupric acetate selective receptor derived from alanyl glycoconjugate and their application in selective oxidation of benzylic alcohols

• Published in: Catalysis communications 2012-11, Vol.28, p.120-123
• Main Authors: Sah, Ajay K., Soni, Kiran
• Format: Article
• Language: English
• Subjects: Copper; Fluorescence; Glucopyranosylamine; Oxidation; TEMPO
• ISSN: 1566-7367; 1873-3905
• DOI: 10.1016/j.catcom.2012.08.024

Cupric acetate sensing ability of alanyl-(4,6-O-ethylidene-β-D-glucopyranosylamine) derived receptor (L-N2O2) has been explored using fluorescence and UV–visible absorption spectroscopy. Cupric acetate quenches the fluorescence intensity of L-N2O2 with a correlation coefficient, R=0.978 and Stern Volmer constant, KSV=38,067M−1 revealing the possibilities of interaction via dynamic mode. Further, copper complex of L-N2O2 has been utilized in selective oxidation of primary and secondary alcohols into the corresponding carbonyl compounds. Alanyl-(4,6-O-ethylidene-β-D-glucopyranosylamine) derived novel receptor has been synthesized, which interacts with cupric acetate selectively and the resultant complex oxidizes primary and secondary alcohols into corresponding carbonyl compounds. [Display omitted] ► First report on L-alanyl-4,6-O-ethylidene-β-D-glucopyranosylamine derived receptor. ► The receptor selectively interacts with cupric acetate. ► Cupric acetate solution quenches the emission band of receptor at 424nm in MeOH. ► Co-association of receptor and cupric acetate acts as selective oxidizing agent.