Unified synthesis of multiply arylated alkanes by catalytic deoxygenative transformation of diarylketones

Abstract

A deoxygenative transformation of diarylketones leading to multiply arylated alkanes was developed. Diarylketones were reacted with diphenylphosphine oxide resulting in a phospha-Brook rearrangement, followed by palladium-catalyzed cross-couplings or a Friedel–Crafts...

New Synthesis of Diarylmethanes, Key Building Blocks for SGLT2 Inhibitors

“…The reduction protocol was applied to the synthesis of diarylmethanes ( 1b (bromide), 1c , 1d , 1e ) for canagliflozin ( 3a ), empagliflozin ( 3c ), and luseogliflozin ( 3d ) to give the desired products in good yields (Table , entries 1, 3, and 4). In marked contrast, when reduction of diarylketone ( 5c ) corresponding to dapagliflozin ( 3b ) was examined, the reaction gave a dimer 7c (Table , entry 2) …”

Electrochemical Reduction of Diarylketones and Aryl Alkenes

“…It is noteworthy that the electrochemical reduction system was applied utilizing 4-benzoylbiphenyl (2f), oxygen hybrid xanthene (2o), and sulfur hybrid thioxanthene (2p). The identity of all resultant products was verified using proton and carbon nuclear magnetic resonance spectroscopy ( 1 H and 13 C NMR) (as depicted in Figures S2-S37). Unfortunately, this reducing system proved ineffective for the reduction of alkyl ketones, aldehydes, and monoaryl ketones (as described in Scheme S2).…”

“…Selective hydrogenation reactions of ketones and alkenes are of high priority among numerous chemical transformations due to their broad range of applications, encompassing both natural products to food industries. [12] Over the past several decades, various transition metal catalysts driven by noble metals such as Pd, [13] Ru, [14] Ir, [15] and Rh, [16] as well as earthabundant metals such as Zn, [17] Ni, [18] Cu, [19] Co, [20] Fe, [21][22][23] and Mn, [24] have been developed and utilized in the hydrogenation of C=O or C=C bonds (Scheme 1A). These homogeneous catalytic systems possess exceptional properties and exhibit high turnover, but the precise design of ligands, the need for metals with low natural abundance, and the challenge of removing and recovering synthetic catalysts all contribute to increased difficulty and cost in an industrial setting.…”

Visible-light-induced tandem ring opening/1,6-conjugate addition of cyclobutanols with p-quinone methides under metal- and additive-free conditions

“…1 Consequently, substantial efforts have been made for the construction of diaryl ketone skeletons and significant achievements have been gained in recent years. 2 Nevertheless, in contrast to the proximal diaryl ketones such as α,α- and β,β-diaryl ketones that can be easily prepared through ortho electrophilic substitution or α,β-Michael addition of unsaturated ketones, 3 synthetic strategies to access the distal diaryl ketones (γ,γ- and δ,δ-) are surprisingly rare and considered challenging. In 2019, Hong and coworkers 4 provided a new strategy to achieve γ,γ- and δ,δ-diaryl ketones via a palladium( ii )-catalyzed 1,1-difunctionalization of simple alkenes (Scheme 1a, right).…”