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Beilstein J. Org. Chem. 2022, 18, 1055–1061, doi:10.3762/bjoc.18.107
Graphical Abstract
Scheme 1: Designed electrochemical hydrogenation of enones 1 with a PEM reactor.
Figure 1: Electrochemical setup of the PEM reactor: a) Electrochemical reduction system with the PEM reactor....
Figure 2: Reaction profile of the electrochemical hydrogenation of 1a with a PEM reactor using a) Pd/C and b)...
Scheme 2: Electrochemical hydrogenation of several enones 1 with a circulating PEM reactor using a Pd/C catho...
Scheme 3: Electrochemical hydrogenation of several enones 1 with a circulating PEM reactor using an Ir/C cath...
Scheme 4: Mechanistic studies.
Scheme 5: Electroreduction of 1a with the circulating PEM reactor using H2O as a proton source.
Beilstein J. Org. Chem. 2018, 14, 1192–1202, doi:10.3762/bjoc.14.100
Scheme 1: Generation and reaction of cationic species generated by “indirect cation pool” methods.
Figure 1: (a) 1H NMR of N-acyliminium ion C1 in CD2Cl2 at −80 °C (600 MHz). (b) Preferred conformation of C1.
Figure 2: (a) 1H NMR spectrum of C3 in CD2Cl2 at −60 °C (400 MHz). (b) Preferred conformation of C3.
Figure 3: (a) 1H NMR spectrum of C5 in CD2Cl2 at −60 °C (400 MHz). (b) Preferred conformation of C5.
Figure 4: Summary of the conformations of N-acyliminium ions C1–C6.
Figure 5: Stevens’ hypothesis on the tendency of the addition of nucleophiles to N-acyliminium ions. The subs...
Figure 6: A plausible mechanism of the observed diastereoselective reaction of the N-acyliminium ions.
Figure 7: Comparison of ΔG for the pseudo-equatorial and pseudo-axial conformations of C1–C6 at the B3LYP/6-3...