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1 article(s) from Lupidi, Gabriele

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

Sebastien Curpanen,
Per Reichert,
Gabriele Lupidi,
Giovanni Poli,
Julie Oble and
Alejandro Perez-Luna

Beilstein J. Org. Chem. 2022, 18, 1256–1263, doi:10.3762/bjoc.18.131

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Scheme 1: C3–Si bond functionalization of biomass-derived 3-silylated furfural platforms.

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Scheme 2: Preparation of 3-silylated 2-furyl carbinols.

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Scheme 3: C–Si bond functionalization of 2,3-disubstituted furyl carbinols by 1,4-silyl migration.

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Scheme 4: Attempts of C3–Si bond functionalization promoted by intramolecular activation via alkoxide.

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Scheme 5: Alkoxide-promoted cyclic siloxane formation from 2-[(3-benzyldimethylsilyl)furyl] carbinol 4c.

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Scheme 6: TBAF-promoted cyclic siloxane formation from 2-[(3-benzyldimethylsilyl)furyl] carbinol 4c.

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Scheme 7: Pd-catalyzed arylation of 2-[(3-benzyldimethylsilyl)furyl] carbinol 4c.

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Scheme 8: Cu-catalyzed allylation and methylation of 2-[(3-benzyldimethylsilyl)furyl] carbinols. ^aCuI⋅PPh₃ (1...

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Published 16 Sep 2022

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