Related Experiment Video
Updated: Jul 9, 2026

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
Visible-Light-Induced Hydroxyperfluoroalkylation of Alkenes to Access β-Perfluoroalkyl Alcohols
Yanyan Zhang1, Yongyan Luo1, Mengting Liu1
1Key Laboratory of Theoretical Organic Chemistry and Functional Molecule, Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, China.
None:
The photoinduced metal-free direct hydroxyl perfluoroalkylation of alkenes with perfluoroalkyl iodides (IRf) is achieved. A variety of structurally diverse β-perfluoroalkyl alcohols are produced with olefins in air in high yields. The key to this transformation lies in the electron-donor-acceptor (EDA) generation of N,N,N',N'-tetramethylethane-1,2-diamine (TMEDA) and IRf. It is also characterized by photocatalyst-free design, broad substrate scope, and good functional group tolerance. This reaction can be used for gram-level synthesis and may be applied in drug discovery and organic synthesis. This study also proposes a reasonable reaction mechanism.
Related Concept Videos
Hydroboration-Oxidation of Alkenes
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.
Electrophilic Addition to Alkynes: Hydrohalogenation
Radical Anti-Markovnikov Addition to Alkenes: Overview
Base-Promoted α-Halogenation of Aldehydes and Ketones
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 stereochemistry.
