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Cross-pinacol coupling of two different carbonyl compounds was achieved through successive one-electron transfer processes under photocatalytic conditions. In this process, an umpoled anionic carbinol synthon was generated in situ to react nucleophilically with a second electrophilic carbonyl compound. A wide variety of aromatic and aliphatic aldeh...
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Context 1
... (Fig. 3). The unsymmetric 1,2-diketone 7aA was obtained in 92% yield by Swern oxidation of diol 3aA. 26 A reaction involving a cross-pinacol coupling of 1a and 2a followed by treatment with TsOH afforded ketone 8aA in 45% yield (two steps). The reaction of 3aB with 2,2-dimethoxypropane in the presence of TsOH gave the cyclic acetal 9aB in 96% ...
Context 2
... (Fig. 4a). To elucidate the role of CO2, we performed an electrochemical analysis of aldehyde CO2 0 mL 1 mL saturated 1a by cyclic voltammetry in DMF in the presence or absence of the CO2 additive (Fig. 4c, and SI, Fig. S3). Under a N2 atmosphere, aldehyde 1a showed two successive reduction peaks (Fig. 4c, red). The first reversible reduction peak at -1.51 V (Ep) can be assigned to the first electron transfer to afford the ketyl radical, whereas the second irreversible peak at -2.11 V (Ep) is assigned as a second electron transfer to give the anionic ...
