Borane catalysed ring opening and closing cascades of furans leading to silicon functionalized synthetic intermediates.
basic_science · Level V
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- Record sourced from PubMed, PMID 27892459.
- Also identified by DOI 10.1038/ncomms13431 and PMC identifier 5133710.
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Abstract
The conversion of renewable biomass resources to synthetically valuable chemicals is highly desirable, but remains a formidable challenge in regards to the substrate scope and reaction conditions. Here we present the development of tris(pentafluorophenyl)borane-catalysed conversion of furans via ring-opening and closing cascade processes to afford silicon-functionalized synthetic chemicals under transition metal-free conditions. The furan ring-opening with hydrosilanes is highly efficient (TON up to 2,000) and atom-economical without forming any byproduct to give rise to α-silyloxy-(Z)-alkenyl silanes. Additional equivalents of silane smoothly induce a subsequent B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-catalysed cyclization of initially formed olefinic silane compounds to produce anti-(2-alkyl)cyclopropyl silanes, another versatile synthon being potentially applicable in the synthesis of natural products and pharmacophores.