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

Nat Commun. 2016 Nov 28:7:13431. doi: 10.1038/ncomms13431.

Authors

Chinmoy K Hazra^{1

2}, Narasimhulu Gandhamsetty^{1

2}, Sehoon Park^{1

2}, Sukbok Chang^{1

2}

Affiliations

¹ Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 305-701, South Korea.
² Department of Chemistry, Korea Advanced Institute of Science &Technology (KAIST), Daejeon 305-701, South Korea.

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.

Publication types

Research Support, Non-U.S. Gov't