Deuterated methanol methanol d4

Methanol (MeOH) and n-heptane were purchased from Carlo Erba Reactifs SDS (Val de Reuil, France). Deuterated Methanol (Methanol-d4) was purchased from Sigma-Aldrich (Saint-Quentin-Fallavier, France). An identification number was assigned to each of the investigated species: the common beech Fagus sylvatica (1), the pedunculate oak Quercus robur (2), the black alder Alnus glutinosa (3), the wild cherry Prunus avium (4), the sycamore maple Acer pseudoplatanus (5), the ash Fraxinus excelsior (6), the poplar Populus x canadensis (Robusta) (7), the European larch Larix decidua (8), the Norway spruce Picea abies (9), and the Eurasian aspen Populus tremula (10). The MeOH bark extracts of each tree species were prepared as previously reported [17 (link)]. Barks were collected in the forest of Signy l’Abbaye (Grand Est region, France), in October 2014. After drying at 30 °C for 72 h and grinding by a hammer mill, two successive solid-liquid extractions with 3 L of n-heptane (E1) and then 3 L of MeOH (E2) were performed on 200 g of the powdered barks under magnetic stirring for 24 h at room temperature. The resulting solutions were filtered, and the solvents were evaporated under reduced pressure. As a result, 20 extracts were obtained from E1-1 to E1-10 (n-heptane extracts) and from E2-1 to E2-10 (MeOH extracts).

All of the experimental procedures associated with this work were carried out under nitrogen using standard Schlenk techniques. The solvents used were dried using an Innovative Technology anhydrous solvent system, or distilled from an appropriate drying agent under nitrogen. The catalyst precursor [IrCl(IMes)(COD)] (1) employed in this work was synthesized by established procedures.²⁷ The SABRE experiments undertaken used a variety of concentrations of the substrate and catalyst that are detailed appropriately in the text. Deuterated methanol (methanol-d₄) was purchased from Sigma Aldrich. Nicotinic acid (NA, Sigma Aldrich) and caesium carbonate (Cs₂CO₃) (Alfa Aesar) were used as supplied.

Methanol (MeOH), Methyl-ter-butyl ether (MtBE), ethyl acetate (EtOAc), acetonitrile (CH₃CN) and n-heptane (Hept) were purchased from Carlo Erba Reactifs SDS (Val de Reuil, France). Deuterated methanol (methanol-d₄) was purchased from Sigma-Aldrich (Saint-Quentin, France). Deionized water (H₂O) was used to prepare all aqueous solutions. Synthetic resveratrol was purchased from Sigma-Aldrich (Saint-Quentin, France).