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Chinmoy Kumar Hazra
분자활성 촉매반응 연구단
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Borane catalysed ring opening and closing cascades of furans leading to silicon functionalized synthetic intermediates

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Title
Borane catalysed ring opening and closing cascades of furans leading to silicon functionalized synthetic intermediates
Author(s)
Chinmoy K. Hazra; Narasimhulu Gandhamsetty; Sehoon Park; Sukbok Chang
Publication Date
2016-11
Journal
NATURE COMMUNICATIONS, v.7, no., pp.13431 -
Publisher
NATURE PUBLISHING GROUP
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(C6 F5)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. © The Author(s) 2016
URI
http://pr.ibs.re.kr/handle/8788114/3256
DOI
10.1038/ncomms13431
ISSN
2041-1723
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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