Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)2(mix-BPBP)] and a Combination of H2O2 and NaIO4
Publication date
2015-07-01
Authors
Spannring, Peter
Yazerski, Vital A.
Chen, J.
Otte, Matthias
Weckhuysen, Bert M.
Bruijnincx, Pieter C.A.
Klein Gebbink, Robertus J.M.
Editors
Advisors
Supervisors
Document Type
Article
Metadata
Show full item recordCollections
License
taverne
Abstract
A method for the regioselective transformation of dienes to carbonyl compounds has been developed. Electron-rich olefins react selectively to yield valuable aldehydes and ketones. The method is based on the catalyst [Fe(OTf)2(mix-BPBP)] with an oxidant combination of H2O2 (1.0 equiv.) and NaIO4 (1.5 equiv.); it uses mild conditions and short reaction times, and it outperforms other olefin cleavage methodologies. The combination of an Fe-based catalyst, [Fe(OTf)2(mix-BPBP)], and the oxidants H2O2 and NaIO4 can discriminate between electronically different double bonds and oxidatively cleave the electron-rich bond in dienes to yield aldehydes and ketones in a regioselective manner. The reaction requires mild conditions (0-50 C) and short reaction times (70 min).
Keywords
Hydrogen peroxide, Iron, Olefin cleavage, Oxidation, Regioselectivity, Taverne, Inorganic Chemistry
Citation
Spannring, P, Yazerski, V A, Chen, J, Otte, M, Weckhuysen, B M, Bruijnincx, P C A & Klein Gebbink, R J M 2015, 'Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf) 2 (mix-BPBP)] and a Combination of H 2 O 2 and NaIO 4', European Journal of Inorganic Chemistry, vol. 2015, no. 21, pp. 3462-3466. https://doi.org/10.1002/ejic.201500213