http://www.jsps.org/alumni/documents/JohnFossey20101129.pdf

Boronic acid building blocks: tools for self assembly.

Metal-Free Methods in the Synthesis of Macrocyclic Schiff Bases

The tetrahedral character of the boron atom newly defined—a useful tool to evaluate the N→B bond

The reversibility of boronic acid and diol interaction makes it an ideal candidate for the design of self-assembled molecular structures. Reversibility is required to ensure that the thermodynamically most stable structure is formed. Reversibility also ensures that any errors produced during the assembly process are not permanent.

/pdf/boronic-acids-in-molecular-self-assembly-35x3fuc6gk.pdf

Boronic Acids in Molecular Self‐Assembly

Boronic acids are versatile building blocks for the construction of complex molecular architectures. Using reversible condensation reactions, it is possible to obtain macrocycles, cages, dendritic structures, and rotaxanes, as well as 1-, 2-, and 3-dimensional polymers in one-pot reactions from simple starting materials. This perspective highlights important recent developments in this area.

Boronic acids as building blocks for molecular nanostructures and polymeric materials

A series of 2-salicylideneamino ethanol derivatives with substituents in different positions have been brought to reaction with phenylboronic acid. Depending on the number and position of the substituents in the ligand, three boronate structure types have been obtained. Thereby, it could be shown that the formation of a macrocyclic dimeric boronate is preferred over the monomeric compound and a [5.4.0]heterobicyclic system with a B(4)−O−B(3) structural unit. The three structure types have been analyzed by X-ray crystallography, where a series of parameters such as N→B bond length, torsion angles, tetrahedral character at the boron atom, deviation of the boron atom from the mean plane and sum of bond angles in the heterocyclic rings have been evaluated in order to determine the factors for the preferred formation of each compound. Finally a new synthetic strategy is presented that permits the synthesis of other macrocyclic boronates in the future.

Synthesis and Study of Monomeric and Dimeric Boronates by Spectroscopic Methods and X-ray Crystallography

Arylboronic acids and different salen ligands have been brought to reaction in a 2:1 stoichiometry in ethanol, toluene, and acetonitrile. In all cases bimetallic boronates with chiral boron atoms could be isolated with the difference that in ethanol mostly open bimetallic boronic esters are obtained, while in toluene or acetonitrile closed bimetallic complexes with a central seven- or eight-membered heterocyclic ring are formed. Both structural types have been characterized by spectroscopic techniques and X-ray crystallography showing that the reactions are diastereoselective in the case of the bimetallic heterocyclic structures. The configurations and conformations of the seven- and eight-membered rings are different, and this may depend on steric effects and/or repulsive intramolecular π−π interactions between the two salicylidene moieties attached to the central ring.

Preparation of Seven- and Eight-Membered Boron Heterocycles from Different Salen Ligands and Arylboronic Acids

Triethylborane (TEB) was found to be a mild, efficient, and acid catalyst in electrophilic substitution reaction of indoles with aldehydes compounds to afford the corresponding bis(indolyl)methanes. Vibrindole A (5) and bis(indolyl)methanes derivatives 16 and 18 were synthesized using this methodology. Compound 16 is an intermediary in the synthesis of the natural bisindoles arsindoline B (2) and streptindole (6). The structure of vibrindole A (5) was unequivocally confirmed by a single crystal X-ray diffraction analysis.

/pdf/synthesis-of-bis-indolyl-methanes-catalyzed-by-1dyy5tmrn1.pdf

Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane.

Degradation of contaminants of emerging concern in a secondary effluent using synthesized MOF-derived photoanodes: A comparative study between photo-, electro- and photoelectrocatalysis.

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Papers

Synthesis and Study of Monomeric and Dimeric Boronates by Spectroscopic Methods and X-ray Crystallography

Preparation of Seven- and Eight-Membered Boron Heterocycles from Different Salen Ligands and Arylboronic Acids

Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane.

Degradation of contaminants of emerging concern in a secondary effluent using synthesized MOF-derived photoanodes: A comparative study between photo-, electro- and photoelectrocatalysis.