Related Experiment Video
Updated: Aug 3, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
Recent advances in visible light-induced C(sp 3)-N bond formation
Mónica Rivas1,2,3, Vitalii Palchykov1,3, Xiangqing Jia1,3
1Department of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, TX, USA.
Visible light photoredox catalysis enables efficient synthetic chemists to form carbon-nitrogen bonds. This review covers recent advances in C(sp3)-H amination and cross-coupling reactions using this mild methodology.
Area of Science:
- Organic Chemistry
- Photochemistry
- Synthetic Methodology
Background:
- The formation of carbon-nitrogen (C-N) bonds is crucial in synthesizing pharmaceuticals, natural products, and materials.
- Traditional C-N bond-forming methods often require harsh conditions or lack selectivity.
- Visible light photoredox catalysis has emerged as a powerful tool for mild and efficient organic transformations.
Purpose of the Study:
- To review recent advancements (post-2014) in visible light-induced C(sp3)-N bond formation.
- To highlight the application of photoredox catalysis in C(sp3)-H activation strategies.
- To showcase the utility of these methods in amination of olefins and carbonyl compounds, and cross-coupling reactions.
Main Methods:
- Utilizing visible light to generate reactive radical intermediates under mild conditions.
- Employing photoredox catalysts to convert light energy into chemical energy.
- Focusing on C(sp3)-H functionalization for direct C-N bond construction.
Main Results:
- Significant progress has been made in developing selective C(sp3)-H amination reactions.
- Visible light catalysis facilitates efficient cross-coupling reactions involving C(sp3) centers.
- These photo-driven methods offer a sustainable and efficient alternative to conventional synthetic approaches.
Conclusions:
- Visible light photoredox catalysis is a versatile platform for constructing C(sp3)-N bonds.
- Recent advances have expanded the scope of C(sp3)-H activation for amination and cross-coupling.
- This methodology holds great promise for the synthesis of complex organic molecules.
More Related Videos
09:12[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
Related Concept Videos
Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)
The extent of coupling depends on the C‑C bond length, the two H‑C‑C angles, any electron-withdrawing substituents, and the dihedral angle between the...
IR and UV–Vis Spectroscopy of Aldehydes and Ketones
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
¹H NMR: Long-Range Coupling
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...