Modular Urea‐Based Catalytic Platforms Bearing Flexible Pyridylmethylamine and Rigid Pyridyl‐Imidazolidine Fragments

Abstract

The selective and concise synthesis of new urea‐based catalytic platforms is described. Each platform incorporates a urea or thiourea motif with a pyridylmethylamine or pyridyl‐imidazolidine fragment. These modular catalytic platforms efficiently promote Michael addition reactions. Moreover, the corresponding Cu complexes successfully catalyse Henry‐type reactions.

Design and property investigation on a five-interaction-based fluorescent anion receptor clip

“…Following our interest in non-covalent interactions, 19,20 we focused on the tetrazine ring, which exhibits both excellent photophysical 21–24 and anion–π binding properties. 25,26 We recently showed that photophysical properties are particularly useful to characterize anion complexes in solution in a new anion receptor (1) combining a tetrazine and an urea subunits linked by a short flexible arm.…”

Intertwined Detection and Recognition Roles of Tetrazine in Synergistic Anion‐π and H‐bond Based Anion Receptor

“…Alongside highly pre-organized rigid receptors widely spread in supramolecular chemistry, [15] we focused our attention on single molecules comprising a hydrogen bonding donor linked to a deficient heterocycle able to generate anion-interactions. Based on our recent publications [16][17][18][19][20][21] and publications from Melguizo and Bianchi, [22,23] we envisioned that the combination of urea and tetrazine moieties would be beneficial to anion binding and allow cross-characterisation of binding properties. On one hand, the urea motif would enable gaining information from 1 H NMR techniques and on the second we take benefits from the dual role of the tetrazine fragment acting as anion-acceptor and as fluorescent probe (Scheme 1).…”

Deciphering preferred geometries of pyridylmethylamines-based complexes: A robust strategy combining NMR, DFT and X-ray

“…11 Such compounds revealed especially valuable as catalytic systems in various synthetic organo-and metallo-promoted transformations including oxidative C-C bond formation, cycloaddition reactions, Friedel-Crafts alkylation, Henry reaction, Suzuki coupling, C-H arylation. [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] Figure 1. Pma modulation sites, transition metal and proton complexes and Zn II and Co II complexes.…”