1-benzyl-1,4-dihydronicotinamide (1,4-BNAH) was photochemically produced from BNA+ using cobalt diimino-dioxime catalysts in the presence of metal/organic photosensitizers (PS) and triethanolamine (TEOA) in argon-purged acetonitrile and aqueous solutions. The product yield was determined by using HPLC-UV/Vis (λmax = 355 nm) and the maximum TONs (vs. catalyst) of 31.1 in acetonitrile and 14.8 in water were recorded. Similar product yield was also determined by photoluminescence (λex = 348 nm, λem = 436 nm). Besides, the production of 1,4-BNAH was confirmed by 1H NMR analysis, in which the characteristic doublet of doublet (dd) signal at δ = 3.05 – 3.07 ppm for the methylene protons (CH2) at the 4-position of 1,4-BNAH was observed. 1H NMR performed in CD3CN containing 5% (v/v) D2O showed the dd signal was reduced to a large extent, suggesting that the proton needed in the reaction originated from water. As indicated by the quenching studies, the photoexcited PS* was first reduced to PS•− by TEOA and then reduced the catalyst from the CoIII state to the CoI state, which probably reduced later the BNA+ to 1,4-BNAH by a hydride transfer.

Precious-Metal-Free Photocatalytic Production of an NADH Analogue Using 
 Cobalt Diimine–Dioxime Catalysts Under Both Aqueous and Organic Conditions

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Precious-Metal-Free Photocatalytic Production of an NADH Analogue Using Cobalt Diimine–Dioxime Catalysts Under Both Aqueous and Organic Conditions