Reductive CO 2 Homocoupling: Synthesis of a Borylated C 3 Carbohydrate

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 C 3 ‐carbohydrate from CO 2 as the only source of carbon. This result correspo...

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Bibliographic Details
Published inChemCatChem Vol. 11; no. 2; pp. 760 - 765
Main Authors Béthegnies, Aurélien, Escudié, Yannick, Nuñez‐Dallos, Nelson, Vendier, Laure, Hurtado, John, del Rosal, Iker, Maron, Laurent, Bontemps, Sébastien
Format Journal Article
LanguageEnglish
Published Wiley 23.01.2019
Subjects
Chemical Sciences
Coordination chemistry
carbine
formose
carbohydrate
CO2
borane
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Summary: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 C 3 ‐carbohydrate from CO 2 as the only source of carbon. This result corresponds to the unprecedented formation of a polyol chain and of asymmetric carbon atoms from CO 2 . The adopted strategy involves the Fe‐catalysed selective 4e − reduction of CO 2 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<80 °C, 1 atm of CO 2 ) and short reaction time (t<2 h).
ISSN:1867-3880
1867-3899
1867-3899
DOI:10.1002/cctc.201801875