Selective Oxidation of Alcohols to Carbonyl Compounds Mediated by Fluorous-Tagged TEMPO Radicals
Oxidation of primary, benzylic and secondary alcohols into their corresponding aldehydes and ketones with safe, inexpensive oxidants was achieved in good yields under mild conditions in the presence of catalytic amounts of 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) radicals bearing perfluoroalkyl...
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Published in | Advanced synthesis & catalysis Vol. 347; no. 5; pp. 677 - 688 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
01.04.2005
WILEY‐VCH Verlag Wiley |
Subjects | |
Online Access | Get full text |
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Summary: | Oxidation of primary, benzylic and secondary alcohols into their corresponding aldehydes and ketones with safe, inexpensive oxidants was achieved in good yields under mild conditions in the presence of catalytic amounts of 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) radicals bearing perfluoroalkyl substituents. These “fluorous‐tagged” TEMPOs were readily isolated from the reaction products by liquid‐liquid or solid‐phase extraction, considerably simplifying the purification step. Their recyclability was strongly influenced by the nature of the oxidizing system. The best results were obtained using either [bis(acetoxy)iodo]benzene (BAIB) or aqueous NaOCl as the primary oxidants. Fluorous TEMPO 10 could be reused up to six times in the BAIB oxidation of 1‐octanol with only minor loss of catalytic activity. |
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Bibliography: | ark:/67375/WNG-SGMQW65L-R ArticleID:ADSC200404343 istex:597BD1CA02D3F856E685F5886004E4AE0D170459 |
ISSN: | 1615-4150 1615-4169 |
DOI: | 10.1002/adsc.200404343 |