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Volumn 356, Issue 17, 2014, Pages 3563-3574

Copper catalysts for selective c-c bond cleavage of b-o-4 lignin model compounds

Author keywords

Aerobic oxidation; C C bond cleavage; Copper catalysts; Lignin models; TEMPO 2,2,6,6 tetramethyl piperidin 1 yl oxyl

Indexed keywords


EID: 84915758505     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400463     Document Type: Article
Times cited : (60)

References (90)
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  • 76
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    • Use of the catalyst systems optimized previously by Mark et al. (CuCl, 1,10-phenanthroline, N-Me-imidazole, KO-t-Bu and diazo H acceptor)[20c] and by Sheldon et al. (CuBr2, 2,2'-bipyridine and KO-t-Bu)[20f,g] gave heterogeneous mixtures and no CC bond cleavage
    • Use of the catalyst systems optimized previously by Mark et al. (CuCl, 1,10-phenanthroline, N-Me-imidazole, KO-t-Bu and diazo H acceptor)[20c] and by Sheldon et al. (CuBr2, 2,2'-bipyridine and KO-t-Bu)[20f,g] gave heterogeneous mixtures and no CC bond cleavage
  • 77
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    • Excess bidentate ligand (ca. 5 equiv. per Cu) was employed to ensure catalyst solubility and adequate solution basicity
    • Excess bidentate ligand (ca. 5 equiv. per Cu) was employed to ensure catalyst solubility and adequate solution basicity
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    • We note however that the five-coordinate Cu(II) aquo tris(2-methylaminoethyl)amine dication is an ineffective oxidation catalyst for lignin models
    • We note however that the five-coordinate Cu(II) aquo tris(2-methylaminoethyl)amine dication is an ineffective oxidation catalyst for lignin models
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    • While authentic b-O-4 lignin models always have OH or OR trans to the benzylic carbon, work by Gold et al.[ 18] showed that the 3,5-dimethoxylated aryl ring model used here gave similar oxidation products. We employed a 13C-labeled version of 1a in previous work[16a] and wanted to compare our results here with the analogous substrate
    • While authentic b-O-4 lignin models always have OH or OR trans to the benzylic carbon, work by Gold et al.[18] showed that the 3,5-dimethoxylated aryl ring model used here gave similar oxidation products. We employed a 13C-labeled version of 1a in previous work[16a] and wanted to compare our results here with the analogous substrate


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