Journal
CARBOHYDRATE POLYMERS
Volume 181, Issue -, Pages 1206-1212Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carbpol.2017.12.012
Keywords
Modified chitosan; Solid-state C-13 NMR; Heterogeneous catalysis; Copper; Henry reaction
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Funding
- Universidade Federal de Ouro Preto (UFOP)
- Fundacao de Amparo a Pesquisa do Estado de Minas Gerais (FAPEMIG) [CEX-APQ-01764-14]
- Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq PVE) [400739/2014-3]
- Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq) [448346/2014-1]
- ANR [ANR-11-BS07-030-01]
- LabEx CHARMMMAT [ANR-11-LABEX-0039]
- University of Versailles St Quentin
- FAPEMIG
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The preparation, characterisation and application of two pyridine-modified chitosan derivatives (C1 and C2) containing Cu(OAc)(2) adsorbed as catalysts for the conversion of benzaldehyde into 2-nitro-1-phenylethanol are described. Quantitative solid-state C-13 multiple-contact cross-polarization, magic-angle-spinning, nuclear magnetic resonance (MC-CP MAS NMR) measurements confirmed the successful grafting of 2-pyridinecarboxaldehyde and 6-methylpyridine-2-carboxaldehyde to the chitosan backbone and indicated that 47(+/- 2)% of the NH2 groups were grafted for both C1 and C2. The use of C1-Cu(OAc)(2) as a catalyst in the nitroaldol reaction led to 96(+/- 1)% conversion and 19(+/- 4)% enantiomeric excess (ee), while the use of C2-Cu(OAc)(2) as a catalyst also promoted the nitroaldol reaction, affording almost quantitatively the expected 2-nitro-1-phenylethanol (98(+/- 1)%) with 14.5(+/- 1.5)% ee.
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