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

• a wide range of transformations [7][8]. Moreover, they proposed a plausible mechanism for the aforementioned conversions (Scheme 2). Initially, an NaI/PPh3 complex I was formed through a cation–π interaction. Subsequently, the combination of complex I with N-(cyclohexanecarbonyloxy)phthalimide

Unraveling the role of prenyl side-chain interactions in stabilizing the secondary carbocation in the biosynthesis of variexenol B

• Moe Nakano,
• Rintaro Gemma and
• Hajime Sato

Beilstein J. Org. Chem. 2023, 19, 1503–1510, doi:10.3762/bjoc.19.107

• possibility of through-space interactions with prenyl side chains using DFT calculations. Our calculations show that (i) the unstable secondary carbocation is stabilized by the cation–π interaction from prenyl side chains, thereby lowering the activation energy, (ii) the four-membered ring formation is

• completed through bridging from the exomethylene group, and (iii) the annulation from the exomethylene group proceeds in a barrier-free manner. Keywords: biosynthesis; carbocation; cation–π interaction; DFT; terpene; Introduction Terpene/terpenoids are most abundant natural products in nature, more than

• carbocation and the prenyl side chain. Figure 1 shows the computed biosynthetic pathway and energy diagram without cation–π interaction, while Figure 2 shows the computed biosynthetic pathway including cation–π interaction from the prenyl side chain. Our research started with the application of DFT

Halides as versatile anions in asymmetric anion-binding organocatalysis

• Lukas Schifferer,
• Martin Stinglhamer,
• Kirandeep Kaur and
• Olga García Macheño

Beilstein J. Org. Chem. 2021, 17, 2270–2286, doi:10.3762/bjoc.17.145

• excellent yields and enantioselectivities up to 95% and 98% ee, respectively. Cation–π interaction: expanding the functionality of hydrogen bond donor catalysts: The development of hydrogen bond donor anion-binding catalysts mainly focuses on the interaction and binding properties towards the anionic

• , and c) asymmetric Mannich synthesis of α-amino esters. Thiourea-catalyzed enantioselective polycyclization reaction of hydroxylactams 51 through cation–π interaction. Enantioselective aza-Sakurai cyclization of hydroxylactams 56 implicating additional cation–π and Lewis base activation

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• -selective cation–π interaction (Scheme 27) [60]. In this study, they used already discussed formylsumanene 66 and aminosumanene 114 prepared from nitrosumanene through the reduction of 80 with Pd/C/H2. As can be seen from Scheme 27, these attractive building blocks 66 and 114 were then converted into the

Synthesis, docking study and biological evaluation of ᴅ-fructofuranosyl and ᴅ-tagatofuranosyl sulfones as potential inhibitors of the mycobacterial galactan synthesis targeting the galactofuranosyltransferase GlfT2

• Marek Baráth,
• Jana Jakubčinová,
• Zuzana Konyariková,
• Stanislav Kozmon,
• Katarína Mikušová and
• Maroš Bella

Beilstein J. Org. Chem. 2020, 16, 1853–1862, doi:10.3762/bjoc.16.152

• –GlfT2 interactions are depicted as dashed lines (yellow – hydrogen bonds, magenta – salt bridge, green – cation/π interaction). The Mg2+ ion is shown as a purple sphere. TLC analysis of the effects of the target compounds at 500 μM on the production of lower lipid-linked galactan precursors. CON

The reductive decyanation reaction: an overview and recent developments

• Jean-Marc R. Mattalia

Beilstein J. Org. Chem. 2017, 13, 267–284, doi:10.3762/bjoc.13.30

• iminyl anion intermediate 27. The latter easily isomerizes to its isomer 28 where a sodium cation–π-interaction occurs. The last step involves a C–C bond cleavage and proton transfer with elimination of NaCN (Scheme 12). This proton transfer occurs with retention of configuration as experimentally

From supramolecular chemistry to the nucleosome: studies in biomolecular recognition

• Marcey L. Waters

Beilstein J. Org. Chem. 2016, 12, 1863–1869, doi:10.3762/bjoc.12.175

• (after Sara Butterfield) [33], Sarah–Zachtide – which investigates a carbohydrate–π interaction (after Sarah Kiehna and Zachary Laughrey) [27][28], Bobtide – which contains a cation–π interaction with KMe3 (trimethyllysine) and was the most stable β-hairpin reported at the time (after Robert Hughes) [22

(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers

• Giorgos Koutoulogenis,
• Nikolaos Kaplaneris and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2016, 12, 462–495, doi:10.3762/bjoc.12.48

• ion intermediate through a stabilizing cation–π-interaction. They came to this conclusion, after an extensive catalyst screening. In 2014, Shi and co-workers presented the synthesis of products 243, utilizing substrates 244 and α,β-unsaturated aldehyde 245. Chiral phosphine organocatalyst 246 was

My maize and blue brick road to physical organic chemistry in materials

• Anne J. McNeil

Beilstein J. Org. Chem. 2016, 12, 229–238, doi:10.3762/bjoc.12.24

• , might be gelators. We searched the CSD for molecules containing a mercury atom (Hg2+) that was involved in an intermolecular cation–π interaction [28]. We identified molecule 2a, which exhibited 1D π–cation–π interactions in the solid state (Figure 3). Graduate student Kelsey (King) Carter synthesized

• just three compounds before gelator 2b was discovered. Single crystals of 2b revealed a surprising 1D π-stacking interaction, rather than the expected cation–π interaction. Nevertheless, powder X-ray diffraction (PXRD) analysis revealed that the packing within the single crystal was not representative

Anthracene coupled adenine for the selective sensing of copper ions

• Kumaresh Ghosh and
• Tanushree Sen

Beilstein J. Org. Chem. 2010, 6, No. 44, doi:10.3762/bjoc.6.44

• the peaks for anthracene moiety is small compared to that in the case of 1 with Cu2+ thereby suggesting a relatively weak cation-π interaction with the anthracenyl function, situated at the distal position from the interacting region. Such findings in the ground state were not observed in case of

• other cations even with Ag+ (Figure 10a for receptor 2). This was also found for 1 with Ag+ ions (Figure 10b). The resulting isotherm fits nicely a 1:1 binding model (Supporting Information File 1). However, the cation-π interaction in both 1 and 2 is due solely to the presence of adenine moiety which

• compared to the cases of 1 and 2 with Cu2+. During the interaction process no other changes were observed. This finding thus indicates that the adenine moiety in both 1 and 2 acts as a metal ion binding site for which participation of anthracene in cation-π interaction is facilitated upon binding of metal

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

• energies range from 22 kJ/mol (neutral hydrogen bonds between water molecules) up to 163 kJ/mol (anionic F–H–F− complex) [10]. Quaternary ammonium ions cannot be bound by hydrogen bonds. 2) Cation–π-interaction [11] The first experimental evidence of interactions between cations and aromatic π-systems came

The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate

• Shlomo Levinger,
• Ranjeet Nair and
• Alfred Hassner

Beilstein J. Org. Chem. 2008, 4, No. 32, doi:10.3762/bjoc.4.32

• as decisive for the remote transmission of chirality. Keywords: cation–π interaction; conjugate addition; diastereoselectivity; regioselectivity; remote chiral induction; Introduction Recently we have disclosed a pathway for remote asymmetric induction in conjugate additions involving lithiated α