Home
Resources
Publications
Multicomponent Assembly of Boron-Based Dendritic Nanostructures

Multicomponent Assembly of Boron-Based Dendritic Nanostructures

Nicolas Christinat, Rosario Scopelliti, Kay Severin

J Org Chem. 2007 Mar 16;72(6):2192-200.

PMID: 17315935

Abstract:

A new synthetic strategy for the construction of boron-based macrocycles and dendrimers is described. Condensation of aryl- and alkylboronic acids with 3,4-dihydroxypyridine is shown to give pentameric macrocycles in which five boronate esters are connected by dative B-N bonds. Three macrocycles have been characterized crystallographically. The boron atoms of these assemblies represent chiral centers, and the assembly process is highly diastereoselective. Attachment of amino or aldehyde groups in the meta position of the arylboronic acid building blocks does not interfere with macrocyclization. This allows performing multicomponent assembly reactions between functionalized boronic acids, dihydroxypyridine ligands, and amines or aldehydes, respectively. Reaction of 3,5-diformylphenylboronic acid, 3,4-dihydroxypyridine, and a primary amine R-NH2 (R=Ph, Bn) gives dendritic nanostructures having a pentameric macrocyclic core and 10 amine-derived R groups in their periphery. Combination of 3,5-diformylphenylboronic acid with 2,3-dihydroxypyridine and the dendron 3,5-(benzyloxy)benzylamine, on the other hand, results in formation of a dendrimer with a tetrameric macrocyclic core and eight dendrons in its periphery.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP480424622	3,5-Diformylphenylboronic acid		480424-62-2	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: