Enantioselective synthesis of β-aryl-γ-lactam derivatives via Heck–Matsuda desymmetrization of N-protected 2,5-dihydro-1H-pyrroles

• Arnaldo G. de Oliveira Jr.,
• Martí F. Wang,
• Rafaela C. Carmona,
• Danilo M. Lustosa,
• Sergei A. Gorbatov and
• Carlos R. D. Correia

Beilstein J. Org. Chem. 2024, 20, 940–949, doi:10.3762/bjoc.20.84

• commercial drug baclofen as hydrochloride. Keywords: desymmetrization; enantioselective Heck–Matsuda reaction; lactam synthesis; N,N-ligands; palladium; Introduction Desymmetrization reactions consist in the modification of a molecule with the loss of one or more symmetry elements, such as those which

• before. Before exploring the reactivity of the olefin towards other aryldiazonium salts, we performed a brief optimization of the process by testing several other N,N-ligands. Therefore, five other N,N-ligands were evaluated as follows: PyraBox (L2), QuinOx (L3), PyOx L4 and L5, and PyriBOx (L6) (Figure

• ,N-ligands. Therefore, we decided to maintain our initial conditions using Pd(TFA)2 and proceeded to the evaluation of the scope of the Heck–Matsuda arylation as shown in Scheme 4. Gratifyingly, the new reaction conditions with the tosylpyrroline 1b showed significant improvements in yield and

Recent advances in phosphorescent platinum complexes for organic light-emitting diodes

• Cristina Cebrián and
• Matteo Mauro

Beilstein J. Org. Chem. 2018, 14, 1459–1481, doi:10.3762/bjoc.14.124

• the energetic destabilization of quenching MC states [45][46]. Complexes based on C^N^N ligands Following the seminal work of von Zelewski [47][48] on platinum(II) complexes bearing C-deprotonated 2-phenylpyridines (C^N), the development of tridentate analogues has received a great deal of attention

• 24.0 cd A−1 and EQE of 7.2%. Alternatively, these compounds were successfully employed in the fabrication of organic memories, which demonstrates the great versatility of this class of platinum(II)-containing materials. Complexes based on bis-anionic C^N^C and N^N^N ligands In an attempt to further

• , dianionic tridentate N^N^N ligands bearing pyrazolate [69], triazolate [69][70][71][72][73] or tetrazolate [74] units have been used to successfully prepare highly luminescent neutral platinum(II) complexes in dilute solution and/or as aggregated state. Due to their promising emitting features, these

Highly bulky and stable geometry-constrained iminopyridines: Synthesis, structure and application in Pd-catalyzed Suzuki coupling of aryl chlorides

• Yi Lai,
• Zhijian Zong,
• Yujie Tang,
• Weimin Mo,
• Nan Sun,
• Baoxiang Hu,
• Zhenlu Shen,
• Liqun Jin,
• Wen-hua Sun and
• Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 213–221, doi:10.3762/bjoc.13.24

• reactions with the advantage of convenient synthetic methods, easy functional group modifications and better stability [37][38][39][40][41][42][43]. Pyridine, azole and imine-based N(sp2) ligands received considerable attention, especially bidentate N,N-ligands. In general, most bidentate N,N(sp2) ligands

Screening of ligands for the Ullmann synthesis of electron-rich diaryl ethers

• Nicola Otto and
• Till Opatz

Beilstein J. Org. Chem. 2012, 8, 1105–1111, doi:10.3762/bjoc.8.122

• at specific time intervals (2 h 15 min and 24 h). In the short-term screening, promising results were obtained with N,P-chelating phosphinite ligands such as L19 and L20, amino acid-derived N,O-ligands such as L2 and L3 and N,O- and N,N-ligands with a rigid backbone such as 8-aminoquinoline (L44) and

• catalytic activity than N,N-dimethylglycine (L1). In the long-term screening, the ligands L2, L43 and L48 were found to exhibit only slightly lower catalytic activity than L1 in the model reaction. In conclusion, N-methylated amino acid-derived N,O-ligands, N,N-ligands with small bite angles, and N