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Fluorous Biphasic Catalytic Oxidation of Sulfides by Molecular Oxygen/2,2‐Dimethylpropanal
Author(s) -
Colonna Stefano,
Gaggero Nicoletta,
Montanari Fernando,
Pozzi Gianluca,
Quici Silvio
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200101)2001:1<181::aid-ejoc181>3.0.co;2-3
Subject(s) - chemistry , catalysis , sulfoxide , substrate (aquarium) , sulfone , cobalt , molecular oxygen , aryl , oxygen , alkyl , medicinal chemistry , catalytic cycle , organic chemistry , polymer chemistry , photochemistry , oceanography , geology
The use of perfluoroalkyl‐substituted cobalt complexes as catalysts for the oxidation of alkyl aryl sulfides with molecular oxygen/2,2‐dimethypropanal has been studied in a fluorous organic biphasic system. The addition of very small amounts of a Co II −tetraarylporphyrin (Co‐ 4 ) led to increased substrate conversions (67−100%). Sulfoxide was generally obtained as the main product, together with variable quantities of sulfone (0−100%), depending on the nature of the substrate. A perfluoroalkyl‐substituted Co II −phthalocyanine (Co‐ 6 ) proved to be less efficient with regard to substrate conversion (40−78%), but afforded sulfoxides selectively. Although the mechanism has not been investigated in detail, the reaction probably proceeds through a free‐radical oxidative process, initiated by the Co II complexes. The attempts at recycling the catalysts through phase separation were partly ineffectual owing to their instability under the reaction conditions, which is more pronounced in the case of Co‐ 6 .