Related Experiment Video
Updated: Sep 19, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
The boron effect on radical difluoromethylation of N-sulfonyl cyclic ketimines
Yu-En Huang1, Kakeru Konagaya1, Shigekazu Ito1
1Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Institute of Science Tokyo (Science Tokyo), 2-12-1-H-113 Ookayama, Meguro-ku, Tokyo 152-8552, Japan. ito@mct.isct.ac.jp.
Abstract:
The intermediary-produced difluoromethyl radical, produced by one-electron oxidation of difluoromethylborates [pinB(Aryl)CF2H][K(18-cr-6)] (pinB = 4,4,5,5-tetramethyl-1,3,2λ2-dioxaborolane) using photo-redox catalysts (PCs), is advantageous for converting N-sulfonyl cyclic ketimines to the corresponding difluoromethylated benzene-fused γ-sultams. Several mechanistic studies indicated the considerable interaction between the difluoromethyl radical and aryl boronate (Ar-Bpin), which would promote the difluoromethylation of the cyclic imine unit. The particular (catalytic) effect of Ar-Bpin was qualitatively supported by characterizing the facilitation of the PC-mediated difluoromethylation with sodium difluoromethanesulfinate (HCF2SO2Na).
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
Radical Substitution: Allylic Bromination
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Hydroboration-Oxidation of Alkenes
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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.