Beilstein J. Org. Chem.2022,18, 1256–1263, doi:10.3762/bjoc.18.131
biomass-derived furfural and 5-methylfurfural, are converted into 3-silylated 2-furylcarbinols upon condensation with organomagnesium or organolithium reagents. The hydroxy unit of the carbinol adducts can be exploited to promote C3(sp2)–Si bond functionalization through intramolecular activation. Two
carbinols from renewable feedstock.
Keywords: biomass; copper; cyclic siloxanes; 2-furylcarbinols; silicon; Introduction
Progress towards the use of nonedible renewable feedstock to replace fossil resources as starting material for high-value chemicals is an important endeavor of modern synthesis [1][2
reactions from C3-silylated furfurals with triorganosilane units have failed so far.
2-Furylcarbinols represent a useful class of furanic synthetic intermediates that have given rise to a number of synthetically relevant transformations, such as the Piancatelli and aza-Piancatelli reactions [16][17] or the
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Graphical Abstract
Scheme 1:
C3–Si bond functionalization of biomass-derived 3-silylated furfural platforms.