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

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 ?-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.

SUBMITTER: Hazra CK

PROVIDER: S-EPMC5133710 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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

Hazra Chinmoy K CK Gandhamsetty Narasimhulu N Park Sehoon S Chang Sukbok S

Nature communications 20161128

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 u ...[more]

PMID: 27892459

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