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Modular synthesis of 2-furyl carbinols from 3-benzyldimethylsilylfurfural platforms relying on oxygen-assisted C–Si bond functionalization

Abstract : 3-Silylated furfurals, readily prepared in three steps from biomass-derived furfural and 5-methylfurfural, are converted into 3-silylated 2-furyl carbinols upon condensation with organomagnesium or organolithium reagents. The hydroxy unit of the carbinol adducts can be exploited to promote C3(sp 2 )–Si bond functionalization through intramolecular activation. Two approaches were contemplated for this purpose. Activation by alkoxides of the C3–SiEt 3 or C3–SiMe 2 t -Bu bonds was ineffective. Conversely, treatment of the C 3-benzyldimethylsilyl-appended derivatives with tetrabutylammonium fluoride led to cyclic siloxanes, which revealed to be competent donors for copper-catalyzed cross-coupling reactions, such as arylation reactions catalyzed by Pd 2 (dba) 3 /CuI, as well as allylation and methylation reactions catalyzed by CuI⋅PPh 3 . C 3-Benzyldimethylsilyl-appended furfurals are thus introduced as versatile platforms, providing a modular access to 3-substituted 2-furyl carbinols from renewable feedstock.
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https://hal.archives-ouvertes.fr/hal-03790431
Contributor : Alejandro Perez Luna Connect in order to contact the contributor
Submitted on : Wednesday, September 28, 2022 - 12:23:47 PM
Last modification on : Wednesday, November 9, 2022 - 4:42:41 PM

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Sebastien Curpanen, Per Reichert, Gabriele Lupidi, Giovanni Poli, Julie Oble, et al.. Modular synthesis of 2-furyl carbinols from 3-benzyldimethylsilylfurfural platforms relying on oxygen-assisted C–Si bond functionalization. Beilstein Journal of Organic Chemistry, 2022, 18, pp.1256-1263. ⟨10.3762/bjoc.18.131⟩. ⟨hal-03790431⟩

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