期刊
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
卷 2, 期 5, 页码 1280-1288出版社
AMER CHEMICAL SOC
DOI: 10.1021/sc500112q
关键词
Carbon dioxide; Mixing; Emulsion; Mass transfer; Allylation; Aqueous media; Biphasic; Sonication; Kinetics
资金
- Engineering and Physical Sciences Research Council
- Birmingham Science City: Innovative Uses for Advanced Materials in the Modern World (West Midlands Centre for Advanced Materials Project)
- Advantage West Midlands
- European Regional Development Fund
- EPSRC [EP/H007784/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/H007784/1] Funding Source: researchfish
Subcritical CO2/H2O (30 degrees C/80 bar) was employed as a renewable solvent mixture in a 1 dm(3) ultrasound reactor. As a representative synthetic transformation, the metal-mediated Barbier allylation was used to demonstrate the facility of formation and separation of the homoallylic alcohol product. The chemoselectivity over the competing aldehyde reduction could be improved by deploying the biocompatible nonionic surfactant Tween 80, a saturated salt aqueous phase, or by carrying out the reaction at 60 degrees C/120 bar. All of these modifications led to an apparent rate increase in the desired allylation. A range of substituted benzaldehydes afforded the corresponding homoallylic alcohols in moderate to high yields. The presence of water constituted a necessary condition for efficient product formation, while CO2 provided an appropriate phase for clean product separation by exploiting a favorable homoallylic alcohol enrichment. In this way, 0.025 mol of homoallylic alcohol product could be isolated from the CO2 phase in 1 h, avoiding further extraction stages that would typically require organic solvents.
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