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Borane catalysed ring opening and closing cascades of furans leading to silicon functionalized synthetic intermediates

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  • Chinmoy K. Hazra

    (Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
    Korea Advanced Institute of Science & Technology (KAIST))

  • Narasimhulu Gandhamsetty

    (Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
    Korea Advanced Institute of Science & Technology (KAIST))

  • Sehoon Park

    (Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
    Korea Advanced Institute of Science & Technology (KAIST))

  • Sukbok Chang

    (Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
    Korea Advanced Institute of Science & Technology (KAIST))

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(C6F5)3-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.

Suggested Citation

  • Chinmoy K. Hazra & Narasimhulu Gandhamsetty & Sehoon Park & Sukbok Chang, 2016. "Borane catalysed ring opening and closing cascades of furans leading to silicon functionalized synthetic intermediates," Nature Communications, Nature, vol. 7(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms13431
    DOI: 10.1038/ncomms13431
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