The stereoselective formation of tetrasubstituted alkenes remains one of the key goals of modern organic synthesis. In addition to other methods, the stereoselective synthesis of tetrasubstituted alkenes can be achieved by means of cross-coupling reactions of electrophilic and nu...
Pipsa Hirva, Petri Turhanen & Juri M. Timonen·Organics·2022
Organoboron compounds are well known for their use as synthetic building blocks in several significant reactions, e.g., palladium-catalyzed Suzuki-Miyaura cross-coupling. As an element, boron is fascinating; as part of a molecule it structurally resembles a three-valent atom, but...
The total synthesis of multifidene, a sex pheromone found in brown algae, is described. The synthesis features the highly enantioselective and diastereoselective addition reaction of an aldehyde to a nitroolefin in the presence of a Hayashi–Jørgensen catalyst and a Nef reaction i...
Michael G. Kallitsakis, Dimitra K. Gioftsidou, Marina A. Tzani, Panagiotis A. Angaridis, Michael A. Terzidis & Ioannis N. Lykakis·Organics·2022
In this study, commercially available molybdenum carbide (Mo2C) was used, in the presence of H2O2, as an efficient pre-catalyst for the selective C-H allylic oxygenation of several unsaturated molecules into the corresponding allylic alcohols. Under these basic conditions, an air...
The catalytic hydrodefluorination (HDF) with a bifunctional azairidacycle using HCOOK was examined for cyano- and chloro-substituted fluoroarenes, including penta- and tetrafluorobenzonitriles, tetrafluoroterephthalonitrile, tetrafluorophthalonitrile, 3-chloro-2,4,5,6-tetrafluoro...
Tatjana Terschüren, Philip Junker, Alexander Schmer, Arturo Espinosa Ferao & Rainer Streubel·Organics·2022
1,2-Bifunctional ligands are rare, in general, which holds especially for those with a P-N linkage. Herein, we report on the synthesis of P-tert-butyl substituted aminophosphane W(CO)5 complexes 3a-f (a: R = R’ = H; b: R = H, R = Me; c: R = H, R’ = ally; d: R = H, R’ = i-Pr; e: R...
Velisaria-Eleni Gerogianni, Giorgos S. Koutoulogenis, Dimitrios Triantafyllos Gerokonstantis & George Kokotos·Organics·2022
Fatty-acid-based nitroalkenes have recently received great attention because of their bioactivities. On the contrary, peptide- or amino-acid-based nitroalkenes have been scarcely explored so far, although they may exhibit interesting biological properties, for example, as enzyme...
Mar Ríos-Gutiérrez, Assem Barakat & Luis R. Domingo·Organics·2022
The [3+2] cycloaddition (32CA) reaction of an azomethine ylide (AY), derived from isatin and L-proline, with phenyl vinyl sulphone has been studied within Molecular Electron Density Theory (MEDT) at the ωB97X-D/6-311G(d,p) level. ELF topological analysis of AY classifies it as a...
Rowan I. L. Meador, Nilamber A. Mate & John D. Chisholm·Organics·2022
N-Alkyl pyrazoles are important heterocycles in organic and medicinal chemistry, demonstrating a wide range of biological activity. A new method for the N-alkylation of pyrazoles has been developed using trichloroacetimidate electrophiles and a Brønsted acid catalyst. These react...
Carla M. Ormachea, María Nélida Kneeteman & Pedro M. E. Mancini·Organics·2022
A number of azaheterocycles (pyridines, pyrroles and indoles) have been properly functionalized so that they can act as dienophiles in cycloaddition Diels–Alder processes. This work analyzed the reactive behavior of these molecules through mechanistic analysis and the regioselect...