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

Chinmoy K. Hazra, Narasimhulu Gandhamsetty, Sehoon Park and Sukbok Chang ()
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Chinmoy K. Hazra: Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
Narasimhulu Gandhamsetty: Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
Sehoon Park: Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
Sukbok Chang: Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)

Nature Communications, 2016, vol. 7, issue 1, 1-9

Abstract: 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.

Date: 2016
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms13431

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DOI: 10.1038/ncomms13431

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