Exploring Coumarins Reduction: NaBH 4 /MeOH versus Nickel Boride Generated In Situ

Autor: Catherine Belle, Amaury du Moulinet d'Hardemare, Clarisse Faure, Hélène Jamet
Přispěvatelé: Département de Chimie Moléculaire (DCM), Université Grenoble Alpes (UGA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR-15-IDEX-0002,UGA,IDEX UGA(2015), ANR-11-LABX-0003,ARCANE,Grenoble, une chimie bio-motivée(2011), ANR-17-EURE-0003,CBH-EUR-GS,CBH-EUR-GS(2017)
Jazyk: angličtina
Rok vydání: 2020
Předmět:
Zdroj: ChemistrySelect
ChemistrySelect, Wiley, 2020, 5 (46), pp.14735-14740. ⟨10.1002/slct.202004038⟩
ISSN: 2365-6549
DOI: 10.1002/slct.202004038⟩
Popis: International audience; The role of reagents NaBH4/MeOH and nickel boride (Ni2B)generated in situ from NaBH4 and NiCl2, are compared in thereduction process of coumarin and a variety of 3,7-substitutedcoumarins bearing electro-donating (ED-group) or electro-withdrawinggroups (EW-group). Coumarins (chromen-2-ones) areonly reduced by Ni2B to the cyclic chromanones. This providesa useful and very simple reduction method for electron-richcoumarins, which are resistant to many other reducingmethods. DFT calculations underlined the role of substituentselectronic effects in the reactivity. Subsequent methanolysismay open the ring to methyl phenylpropanoate esters andalcohols resulting from their reductions can also be produced.
Databáze: OpenAIRE
Externí odkaz: