Palladium on carbon-catalyzed α-alkylation of ketones with alcohols as electrophiles: Scope and mechanism

Abstract

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Bromine radical as a visible-light-mediated polarity-reversal catalyst

“…According to the general procedure A. Colourless liquid (21 mg, 51%). The spectral data is consistent with the literature data (Bennedsen et al, 2019).…”

Tuning the Product Selectivity of the α-Alkylation of Ketones with Primary Alcohols using Oxidized Titanium Nitride Photocatalysts and Visible Light

“…Initially, TiN can catalyze the dehydrogenation of benzyl alcohol to benzaldehyde (entries 1 and 2) on the redox sites of TiN . The presence of KOH is essential for promoting this reaction as benzaldehyde will not generate without KOH in 10 h. Then, condensation between acetophenone and benzaldehyde can occur, which is catalyzed by both KOH and the basic sites of TiN (entries 3–6). ,, Although chalcone is the major product through the aldol condensation, the saturated product dihydrochalcone also exists in a small amount. This is possibly because the hydrogenation of chalcone to dihydrochalcone can proceed without benzyl alcohol (entries 9 and 10).…”

“…A tandem dehydrogenation− condensation mechanism with benzaldehyde as an intermediate has been widely accepted to apply for the direct αalkylation of ketones with alcohols. 47 To determine if this mechanism is also applicable here, kinetics study was conducted for the α-alkylation of acetophenone (1a) with benzyl alcohol (2a) on three representative photocatalysts, the untreated TiN, TiN_350 °C/3 h, and anatase TiO 2 , by recording the conversion of acetophenone and the formation of the products at different reaction times, as given in Figure 6. The kinetics profiles for the three photocatalysts demonstrate that acetophenone and benzyl alcohol were progressively converted into chalcone or dihydrochalcone while no other intermediates were detected by GC during the reaction.…”

Ir-Catalyzed α-Alkylation of Ketones with Alcohols: One-Step Access to Donepezil

“…propan-1-one (5b) 37 Yield: 79.6 mg (71%); white solid; mp 58-60 °C. 1 H NMR (400 MHz, CDCl 3 ):  = 7.86 (d, J = 7.8 Hz, 2 H), 7.31-7.21 (m, 7 H), 3.27 (t, J = 7.7 Hz, 2 H), 3.06 (t, J = 7.6 Hz, 2 H), 2.40 (s, 3 H).…”