Entry to 2-aminoprolines via electrochemical decarboxylative amidation of N‑acetylamino malonic acid monoesters

• Olesja Koleda,
• Janis Sadauskis,
• Darja Antonenko,
• Edvards Janis Treijs,
• Raivis Davis Steberis and
• Edgars Suna

Beilstein J. Org. Chem. 2025, 21, 630–638, doi:10.3762/bjoc.21.50

• feature at Ep = 1.78 V vs Ag/Ag+ (100 mV/s scan rate; see Figure 3A), and the electrolysis of pyrrolidine 6a under the optimized anodic decarboxylative cyclization conditions (entry 8, Table 1) afforded cyclic hemiaminal 12a (33% NMR yield), whose structure was proved by NMR experiments (Figure 3B). The

• undergo the decarboxylative cyclization, but also N-mesyl-protected monoester 9f could be converted into 2-aminoproline derivative 6f in 60% yield using a graphite cathode. However, the N-o-nosyl-protecting group is not compatible with the developed electrolysis conditions, likely because it undergoes an

• , the cyclization of the amino acid fragment-containing monoesters 9l,m afforded dipeptides 6l,m in 36% and 50% yield, respectively. Notably, the decarboxylative cyclization is compatible with the alkene moiety (product 6m). Both dipeptides 6l,m were obtained as a 67:33 mixture of diastereomers. In the

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• photocatalytic decarboxylative radical cascade alkylarylation. Proposed mechanism of the NaI/PPh3-driven photocatalytic decarboxylative radical cascade cyclization. Visible-light-promoted decarboxylative cyclization of vinylcycloalkanes. NaI/PPh3-mediated photochemical reduction and amination of nitroarenes

Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine

• Alessio Regni,
• Francesca Bartoccini and
• Giovanni Piersanti

Beilstein J. Org. Chem. 2023, 19, 918–927, doi:10.3762/bjoc.19.70

• Alessio Regni Francesca Bartoccini Giovanni Piersanti Department of Biomolecular Sciences, University of Urbino, Carlo Bo Piazza Rinascimento 6, 61029 Urbino, PU, Italy 10.3762/bjoc.19.70 Abstract An unusual photoredox-catalyzed radical decarboxylative cyclization cascade reaction of γ,γ

• photocatalyst. Keywords: decarboxylative cyclization; DMAT; ergot alkaloids; photoredox catalysis; radicals; Introduction Visible-light photoredox catalysis is rapidly changing the way organic chemists approach the design and synthesis of molecules by offering new synthetic disconnection opportunities that

• of all ergot alkaloids, specifically the decarboxylative cyclization of DMAT, is still a puzzle even though a radical mechanism has been proposed (Figure 1a) [72][73]. Results and Discussion Herein, we propose that visible light irradiation of the cationic iridium photocatalyst Ir[dF(CF3)ppy]2(dtbbpy

NaI/PPh₃-catalyzed visible-light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides for the efficient synthesis of quaternary oxindoles

• Dan Liu,
• Yue Zhao and
• Frederic W. Patureau

Beilstein J. Org. Chem. 2023, 19, 57–65, doi:10.3762/bjoc.19.5

• terminal alkyne in 3an, and an alkyl chloride in 3ao proved compatible, associated with encouraging yields. In order to further demonstrate the utility of our protocol, a complex scaffold derived from lithocholic acid was tested, and was found to smoothly undergo the decarboxylative cyclization towards

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

• Gagandeep Kour Reen,
• Ashok Kumar and
• Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165