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

Chinmoy K. Hazra; Narasimhulu Gandhamsetty; Sehoon Park; Sukbok Chang

doi:10.1038/ncomms13431

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

Chinmoy K. Hazra, Narasimhulu Gandhamsetty, Sehoon Park, Sukbok Chang^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

54 Scopus citations

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.

Original language	English
Article number	13431
Journal	Nature Communications
Volume	7
DOIs	https://doi.org/10.1038/ncomms13431
State	Published - 28 Nov 2016
Externally published	Yes

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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(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.",

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AU - Hazra, Chinmoy K.

AU - Gandhamsetty, Narasimhulu

AU - Park, Sehoon

AU - Chang, Sukbok

PY - 2016/11/28

Y1 - 2016/11/28

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AB - 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.

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

Abstract

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