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Reductive CO 2 Homocoupling: Synthesis of a Borylated C 3 Carbohydrate
- Source :
- ChemCatChem, ChemCatChem, 2019, 11, pp.760-765. ⟨10.1002/cctc.201801875⟩, ChemCatChem, Wiley, 2019, 11, pp.760-765. ⟨10.1002/cctc.201801875⟩
- Publication Year :
- 2019
- Publisher :
- HAL CCSD, 2019.
-
Abstract
- International audience; To use carbon dioxide as a source of carbon, recent progress has been made toward the synthesis of higher value chemicals and in particular toward Cn compounds. In this context, we report here the synthesis of a borylated C3-carbohydrate from CO2 as the only source of carbon. This result corresponds to the unprecedented formation of a polyol chain and of asymmetric carbon atoms from CO2. The adopted strategy involves the Fe-catalysed selective 4e− reduction of CO2 into bis(boryl)acetal followed in one-pot by a carbene-mediated C−C coupling reaction. Boron is shown to play a key role in the coupling step enabling to observe the first diastereoselective formose-type reaction. This result is in addition obtained under mild reaction conditions (T
- Subjects :
- 010405 organic chemistry
Chemistry
formose
Organic Chemistry
Borane
Carbohydrate
010402 general chemistry
01 natural sciences
Catalysis
0104 chemical sciences
Inorganic Chemistry
chemistry.chemical_compound
13. Climate action
carbohydrate
Organic chemistry
Carbine
CO2
[CHIM.COOR]Chemical Sciences/Coordination chemistry
Physical and Theoretical Chemistry
carbine
borane
Subjects
Details
- Language :
- English
- ISSN :
- 18673899
- Database :
- OpenAIRE
- Journal :
- ChemCatChem, ChemCatChem, 2019, 11, pp.760-765. ⟨10.1002/cctc.201801875⟩, ChemCatChem, Wiley, 2019, 11, pp.760-765. ⟨10.1002/cctc.201801875⟩
- Accession number :
- edsair.doi.dedup.....ec7bb66f31ac086698c148c9f101bede
- Full Text :
- https://doi.org/10.1002/cctc.201801875⟩