Related Experiment Video
Updated: Jan 31, 2026

Negative Additive Manufacturing of Complex Shaped Boron Carbides
Published on: September 18, 2018
Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition
Guido Barzanò1, Alexis Cheseaux1, Xile Hu1
1Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering , Ecole Polytechnique Fédérale de Lausanne (EPFL) , ISIC-LSCI, BCH 3305, Lausanne 1015 , Switzerland.
Abstract:
Z-Selective synthesis of vinyl boronates is challenging. This work describes Fe-catalyzed addition of alkyl radicals, formed by the corresponding alkyl halides, to ethynyl ethynylboronic acid pinacol ester that gives rise to Z-vinyl boronates in high stereoselectivity. The method works best for tertiary and secondary alkyl iodides. The Z-vinyl boronate products are easily converted to other Z-alkenes by transformation of the boronate group. The method is applied for the formal total synthesis of a 5-HT2c receptor agonist.
More Related Videos
06:49Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
Related Concept Videos
Radical Formation: Addition
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
Base-Catalyzed Aldol Addition Reaction
Acid-Catalyzed Aldol Addition Reaction
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
Radical Anti-Markovnikov Addition to Alkenes: Overview