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From chemRxiv
Sorbonne Université - Faculté des Sciences (Paris VI), Sorbonne University

C3–H Silylation of Furfural Derivatives: Direct Access to a Versatile Synthetic Platform Derived from Biomass

The sustainable production of industry-relevant chemicals, ranging from biofuels to pharmaceuticals, requires the development of efficient functionalization of biomass-derived building blocks, such as furan derivatives. Herein we report directed iridium-catalyzed C3–H silylation of furfural compounds, which grants access to versatile synthetic platforms. This transformation was developed on furfuryl derivatives, using imines as directing groups, and trialkylsilanes or bis(trimethylsilyl)methylsilane as silylating agents, in the presence of a hydride scavenger. Subsequently, fluoride-mediated activation strategies were applied to the C3–SiMe(OSiMe3)2 furfural derivatives. This strategy enables a wide range of transformations, namely arylation, alkenylation, alkynylation, allylation and alkylation, as well as halogenation and trifluoromethylation. A variety of high value-added products were thus easily obtained from the same common C3-silylated furfural platform.
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Published on April 7, 2022
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