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Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H 2 O 2 Combined with Periodate Oxidation
Author(s) -
Mecozzi Francesco,
Dong Jia Jia,
Angelone Davide,
Browne Wesley R.,
Eisink Niek N. H. M.
Publication year - 2019
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/ejoc.201901380
Subject(s) - chemistry , sodium periodate , ozonolysis , dihydroxylation , alkene , periodate , bond cleavage , catalysis , cleavage (geology) , epoxide , organic chemistry , manganese , diol , double bond , medicinal chemistry , enantioselective synthesis , geotechnical engineering , fracture (geology) , engineering
A one‐pot multi‐step method for the oxidative cleavage of alkenes to aldehydes/ketones under ambient conditions is described as an alternative to ozonolysis. The first step is a highly efficient manganese catalyzed epoxidation/ cis ‐dihydroxylation of alkenes. This step is followed by an Fe(III) assisted ring opening of the epoxide (where necessary) to a 1,2‐diol. Carbon–carbon bond cleavage is achieved by treatment of the diol with sodium periodate. The conditions used in each step are not only compatible with the subsequent step(s), but also provide for increased conversion compared to the equivalent reactions carried out on the isolated intermediate compounds. The described procedure allows for carbon–carbon bond cleavage in the presence of other alkenes, oxidation sensitive moieties and other functional groups; the mild conditions (r.t.) used in all three steps make this a viable general alternative to ozonolysis and especially for use under flow or continuous batch conditions.