Related Experiment Video
Updated: Dec 11, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Copper-Catalyzed Defluorinative Borylation and Silylation of gem-Difluoroallyl Groups
Trevor W Butcher1, Jonathan L Yang1, John F Hartwig1
1Department of Chemistry, University of California, Berkeley, California 94720, United States.
Abstract:
Stereodefined (Z)-fluoroalkenes are bioisosteres of amides and synthetic precursors to value-added fluorinated compounds, but their stereoselective synthesis remains challenging. Herein, we report a copper-catalyzed formal SN2' defluorinative borylation of 3-substituted 3,3-difluoropropenes to form 3-fluoroallylboronic esters in high yields with excellent Z/E ratios. The primary 3-fluoroallylboronic esters undergo several synthetic sequences involving SE2' substitutions, SN2' substitutions, and sigmatropic rearrangements to provide tertiary allylic fluorides.
More Related Videos
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
09:58Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Preparation and Reactions of Sulfides
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Hydroboration-Oxidation of Alkenes