Narasaka reaction: Desilylative acylation of 1-alkenylsilanes with acid anhydrides

Synthesis of β-fluorocarboxylic esters via organophotoredox-catalyzed fluoroalkoxycarbonylation of alkenes in EtOH

“…To verify the feasibility of this fluoroalkoxycarbonylation strategy, 2-ethoxy-2-oxoacetic acid 2a was selected as the alkoxycarbonyl radical precursor. To our delight, β-fluorinated carboxylic ester ( 3a ) was obtained when a mixture of Selectfluor, 4-vinyl-1,1′-biphenyl ( 1a ), 2-ethoxy-2-oxoacetic acid ( 2a ), K 2 HPO 4 and rhodamine 6G 14 in methanol at room temperature was irradiated with visible light for 16 h (Table 1, entry 1). When a series of organic photocatalysts were investigated, product 3a was obtained in moderate yields, and 5CzBN 15 gave the highest yield (entries 2–4).…”