Abstract
The defluorosilylation of aryl fluorides to access aryl silanes was achieved under transition-metal-free conditions via an inert C–F bond activation. The defluorosilylation, mediated by silylboronates and KOtBu, proceeded smoothly at room temperature to afford various aryl silanes in good yields. Although a comparative experiment indicated that Ni catalyst facilitated this transformation more efficiently, the transition-metal-free protocol is advantageous from a green chemistry perspective.
Highlights
Organofluorine compounds have been critical over the past few decades in pharmaceutical (Inoue et al, 2020), agrochemical (Ogawa et al, 2020), functional materials (Hiyama, 2000; Babudri et al, 2007; Berger et al, 2011; Liu et al, 2017; Liu et al, 2019) and polymer (Améduri et al, 2020) industries
In 2018, we reported a significant achievement on the C–F bond cleavage of aryl fluorides via defluorosilylation using silylboronates (R3SiBPin) in the presence of potassium tert-butoxide (KOtBu) and a catalytic amount of Ni
We found that the C–F bond activation did not require an Ni catalyst in the case of alkyl fluorides
Summary
Organofluorine compounds have been critical over the past few decades in pharmaceutical (Inoue et al, 2020), agrochemical (Ogawa et al, 2020), functional materials (Hiyama, 2000; Babudri et al, 2007; Berger et al, 2011; Liu et al, 2017; Liu et al, 2019) and polymer (Améduri et al, 2020) industries. One of the most attractive properties of organofluorine compounds is their durability, represented by Teflon®, induced by the most vital bond energy of the C–F bond in carbon chemistry (Uneyama et al, 2006; Luo et al, 2007; Amii et al, 2009) Their robustness has often caused severe persistent environmental toxicity, such as the super-greenhouse effect by fluorocarbons (McCulloch et al, 2003; Velders et al, 2007; Shine and Sturges, 2007; Sovacool et al, 2021) and the bioaccumulation of perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS) (Vierke et al, 2012; Stanifer et al, 2018; Chen et al, 2019; Li et al, 2020). While the yields under the catalyst-free conditions were lower than those under Ni-catalysis, the transition-metal-free system is advantageous from the perspective of green chemistry (Scheme 1F)
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