Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 17, Pages 6528-6534Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500121
Keywords
imines; oxidation; photochemistry; regioselectivity; singlet oxygen
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Funding
- Max Planck Society
- DAAD
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Aerobic amine oxidation is an attractive and elegant process for the functionalization of amines. However, there are still several mechanistic uncertainties, particularly the factors governing the regioselectivity of the oxidation of asymmetric secondary amines and the oxidation rates of mixed primary amines. Herein, it is reported that singlet-oxygen-mediated oxidation of 1 degrees and 2 degrees amines is sensitive to the strength of the -CH bond and steric factors. Estimation of the relative bond dissociation energy by natural bond order analysis or by means of one-bond CH coupling constants allowed the regioselectivity of secondary amine oxidations to be explained and predicted. In addition, the findings were utilized to synthesize highly regioselective substrates and perform selective amine cross-couplings to produce imines.
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