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Aerobic Oxidation of Benzylic Alcohols in Water by 2,2,6,6‐Tetramethylpiperidine‐1‐oxyl (TEMPO)/Copper(II) 2‐ N ‐Arylpyrrolecarbaldimino Complexes
Author(s) -
Figiel Paweł J.,
Sibaouih Ahlam,
Ahmad Jahir Uddin,
Nieger Martin,
Räisänen Minna T.,
Leskelä Markku,
Repo Timo
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900478
Subject(s) - chemistry , catalysis , benzaldehyde , copper , hydrogen peroxide , selectivity , benzyl alcohol , alcohol oxidation , alcohol , inorganic chemistry , atmospheric pressure , organic chemistry , photochemistry , oceanography , geology
Novel copper(II) 2‐ N ‐arylpyrrolecarbaldimine‐based catalysts for the aerobic oxidation of benzylic alcohols mediated by the 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) radical are reported. The catalytic activity for both synthesized and in situ made complexes in alkaline water solutions was studied revealing high efficiency and selectivity (according to GC selectivity always >99%) for both of these catalytic systems. For example, quantitative conversion of benzyl alcohol to benzaldehyde can be achieved with the in situ prepared bis[2‐ N ‐(4‐fluorophenyl)‐pyrrolylcarbaldimide]copper(II) catalysts in 2 h with atmospheric pressure of O 2 at 80 °C. Interestingly, these catalysts can utilize dioxygen as well as air or hydrogen peroxide as the end oxidants, producing water as the only by‐product.