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Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

The nature and characteristics of the CH/π interaction are discussed by comparison with other weak molecular forces such as the CH/O and OH/π interaction. The CH/π interaction is a kind of hydrogen bond operating between a soft acid CH and a soft base π-system (double and triple bonds, C6 and C5 aromatic rings, heteroaromatics, convex surfaces of fullerenes and nanotubes). The consequences of CH/π hydrogen bonds in supramolecular chemistry are reviewed on grounds of recent crystallographic findings and database analyses. The topics include intramolecular interactions, crystal packing (organic and organometallic compounds), host/guest complexes (cavity-type inclusion compounds of cyclodextrins and synthetic macrocyclic hosts such as calixarenes, catenanes, rotaxanes and pseudorotaxanes), lattice-inclusion type clathrates (including liquid crystals, porphyrin derivatives, cyclopentadienyl compounds and C60 fullerenes), enantioselective clathrate formation, catalytic enantioface discriminating reactions and solid-state photoreaction. The implications of the CH/π concept for crystal engineering and drug design are evident.

CH/π hydrogen bonds in crystals

Advances in copper complexes as anticancer agents.

This review describes a multidimensional treatment of molecular recognition phenomena involving aromatic rings in chemical and biological systems. It summarizes new results reported since the appearance of an earlier review in 2003 in host-guest chemistry, biological affinity assays and biostructural analysis, data base mining in the Cambridge Structural Database (CSD) and the Protein Data Bank (PDB), and advanced computational studies. Topics addressed are arene-arene, perfluoroarene-arene, S⋅⋅⋅aromatic, cation-π, and anion-π interactions, as well as hydrogen bonding to π systems. The generated knowledge benefits, in particular, structure-based hit-to-lead development and lead optimization both in the pharmaceutical and in the crop protection industry. It equally facilitates the development of new advanced materials and supramolecular systems, and should inspire further utilization of interactions with aromatic rings to control the stereochemical outcome of synthetic transformations.

Aromatic rings in chemical and biological recognition: energetics and structures.

In this manuscript we report a high-level ab initio study of anion−π interactions involving N9-methyl-adenine, N6-methyl-adenine, N9-methyl-hypoxanthine, a dimer of N9-methyl-adenine, and N9,N9‘-trimethylene-bisadenine. DNA bases like adenine are electron-deficient arenes that are well suited for interacting favorably with anions. We demonstrate that these compounds are able to interact favorably with anions. N9-Methyl-adenine, N6-methyl-adenine, and the dimer of N9-methyl-adenine interact with the anion via the six-membered ring more strongly than adenine due to cooperativity effects between the noncovalent π−π and anion−π interactions. This pattern, i.e., coexistence of π−π and anion−π bonding, is observed experimentally in the solid state. Finally, we report the solid-state characterization of two new compounds N6,N6‘-dimethylene-bisadenine hydrochloride and an outer-sphere complex of protonated N9,N9‘-trimethylene-bishypoxanthine with zinc tetrachloride anion, that exhibit interesting anion−π interact...

Anion−π Interactions in Bisadenine Derivatives: A Combined Crystallographic and Theoretical Study

Highly hindered phenolic compounds can be efficiently deoxygenated by reduction of the corresponding triflates under homogeneous [RCOOH, Bu 3 N, PdCl 2 (PPh 3 ) 2 , Ph 2 PCH 2 CH 2 CH 2 PPh 2 , DMF] or heterogeneous (Pd/C) conditions. Reductive deoxygenation under homogeneous conditions has been shown to occur both in the presence of acid (HCOOH, CH 3 COOH, (CH 3 ) 3 CCOOH, PhCH 2 COOH) or in its absence. The concomitant formation of dibutylformamide apparently derives from aminolysis of DMF by dibutylamine, the Pd(0)-catalyzed hydrolysis product of tributylamine. Deuteration experiments suggest that several hydrogen (or deuterium) source operate in the hydrogenolysis processes studied

Deoxygenation of highly hindered phenols

Synthesis, structure and nuclease properties of several ternary copper(II) peptide complexes with 1,10-phenanthroline.

Biological recognition patterns implicated by the formation and stability of ternary metal ion complexes of low-molecular-weight formed with amino acid/peptides and nucleobases/nucleosides

Angel García-Raso

Papers

Anion−π Interactions in Bisadenine Derivatives: A Combined Crystallographic and Theoretical Study

Deoxygenation of highly hindered phenols

Synthesis, structure and nuclease properties of several ternary copper(II) peptide complexes with 1,10-phenanthroline.

Biological recognition patterns implicated by the formation and stability of ternary metal ion complexes of low-molecular-weight formed with amino acid/peptides and nucleobases/nucleosides

Palladium-catalyzed cross-coupling reactions of highly hindered, electron-rich phenol triflates and organostannanes