A molecular canvas for synthesis 'à la carte'

iQUS researchers describe a new method for accessing conjugated dienes in a very simple and effective way, employing a borylated dendralene as the main component.
The method is versatile and functional in that it allows control of the geometry of the double bonds as well as the position of the substituents in the structure.
The results have now been published in Angewandte Chemie.

Conjugated dienes can be found in a wide range of biologically active natural products and functional materials. However, these compounds are also of particular interest given their application in synthetic chemistry. There are currently few methods for successfully accessing highly substituted dienic systems, especially when it comes to introducing different substituents and controlling the geometry of the double bonds.

Sustainable Catalysis and Asymmetric Synthesis Group at Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS) has just described a reaction that results in very efficient conjugated dienes by selective assembly of four components. The main component of this reaction is a borylated dendralene, an easily accessible structure thanks to a catalytic methodology previously developed by the group. “Borylated dendralene is used as a molecular canvas on which, via this new reaction, substituents of a different nature can be introduced a la carte into the dienic system with full control of regioselectivity and stereochemistry” said Prof. Martin Fañanás Mastral, group leader and Principal Investigator at CiQUS.

The new method is versatile in that the position at which each substituent is introduced, as well as the geometry of the double bonds, can be controlled. The functionality that can be introduced into this structure allows subsequent modifications to obtain more complex dyenic structures in a very simple and versatile way. This new method for accessing such compounds has been published in the prestigious journal Angewandte Chemie.

Reference

Eva Rivera-Chao, Martín Fañanás-Mastral. Stereoselective Synthesis of Highly Substituted 1,3-Dienes via “à la carte” Multifunctionalization of Borylated Dendralenes. Angew. Chem. Int. Ed. 2021, 60, 16922–16927.