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Reductive CO 2 Homocoupling: Synthesis of a Borylated C 3 Carbohydrate
Author(s) -
Béthegnies Aurélien,
Escudié Yannick,
NuñezDallos Nelson,
Vendier Laure,
Hurtado John,
del Rosal Iker,
Maron Laurent,
Bontemps Sébastien
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201801875
Subject(s) - chemistry , polyol , context (archaeology) , coupling reaction , boron , acetal , carbon fibers , catalysis , reaction conditions , medicinal chemistry , organic chemistry , combinatorial chemistry , materials science , paleontology , composite material , composite number , polyurethane , biology
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).