Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 48, Pages 17393-17398Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908788
Keywords
aerobic oxidative cleavage; carboxylic acids; C-C bond activation; metal-free NO2 radical catalysts; nitrates
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Funding
- National Natural Science Foundation of China [21733011, 21603236]
- National Key Research and Development Program of China [2017YFA0403103]
- Beijing Municipal Science & Technology Commission [Z181100004218004]
- Chinese Academy of Sciences [QYZDY-SSW-SLH013]
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Stable organic nitroxyl radicals are an important class of catalysts for oxidation reactions, but their wide applications are hindered by their steric hinderance, high cost, complex operation, and separation procedures. Herein, NO2 in DMSO is shown to effectively catalyze the aerobic oxidative cleavage of C(OH)-C bonds to form a carboxylic group, and NO2 was generated in situ by decomposition of nitrates. A diverse range of secondary alcohols were selectively converted into acids in excellent yields in this transition-metal-free system without any additives. Preliminary results also indicate its applicability to depolymerize recalcitrant macromolecular lignin. Detail studies revealed that NO2 from nitrates promoted the reaction, and NO2 served as hydrogen acceptor and radical initiator for the tandem oxidative reaction.
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