Ionic TEMPO in Ionic Liquids: Specific Promotion of the Aerobic Oxidation of Alcohols. Issue 16 (1st August 2016)

• Record Type: Journal Article
• Authors: Hirashita, Tsunehisa; Nakanishi, Makoto; Uchida, Tomoya; Yamamoto, Masakazu; Araki, Shuki; Arends, Isabel W. C. E.; Sheldon, Roger A.
• Is Part Of: ChemCatChem. Volume 8:Issue 16(2016)
• Page Start: 2704
• Page End: 2709
• Publication Date: 2016-08-01
• Subjects: alcohols -- ionic liquids -- oxidation -- oxygen -- radicals; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201600491
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: The main objective of this study was to design a recyclable TEMPO (2, 2, 6, 6‐tetramethylpiperidinyl‐ N ‐oxyl) derivative that could be used as a catalyst in an ionic liquid solvent for the aerobic oxidation of alcohols by using NaNO2 and HCl as co‐catalysts. To this end, a TEMPO derivative bearing a quaternary ammonium group, [4‐Bu2 MeN‐TEMPO][PF6 ] (1 ), was prepared. It was subsequently shown that this ionic TEMPO derivative is an efficient catalyst for the aerobic oxidation of a variety of primary and secondary alcohols. It exhibits a synergistic effect with ionic liquid solvents and readily outperforms analogous oxidations in methylene chloride. Moreover, the ionic TEMPO could be recycled five times with no loss of activity. Abstract : Keeping the TEMPO : A recyclable TEMPO (2, 2, 6, 6‐tetramethylpiperidinyl‐ N ‐oxyl) derivative that can be used as catalyst in ionic liquid solvent for the aerobic oxidation of alcohols by using NaNO2 and HCl as co‐catalysts was designed. This ionic TEMPO derivative is an efficient, recyclable catalyst for the aerobic oxidation of a variety of primary and secondary alcohols.