Related Experiment Video
Updated: May 12, 2026
![[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
09:12
[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Visible light photoredox-catalyzed multicomponent reactions.
1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany. magnus.rueping@rwth-aachen.de
Organic Letters
|April 17, 2013
Summary
New methods enable direct synthesis of α-amino amides and imides from tertiary amines using mild aerobic oxidation. This visible light photoredox catalysis approach functionalizes C(sp(3))-H bonds for diverse, highly functionalized products.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Tertiary amines are versatile building blocks.
- Direct functionalization of C-H bonds remains a significant challenge in organic synthesis.
- Efficient synthesis of α-amino amides and imides is crucial for pharmaceuticals and materials.
Purpose of the Study:
- To develop novel oxidative three-component reactions for direct synthesis of α-amino amides and imides.
- To achieve functionalization of C(sp(3))-H bonds adjacent to nitrogen atoms.
- To establish mild and efficient protocols using visible light photoredox catalysis.
Main Methods:
- Visible light photoredox catalysis.
- Mild aerobic oxidation.
- Three-component reaction strategy involving tertiary amines, isocyanides, and nucleophiles (water or carboxylic acids).
Main Results:
- Successful direct synthesis of α-amino amides and imides from tertiary amines.
- Demonstrated functionalization of C(sp(3))-H bonds adjacent to nitrogen.
- Broad applicability to various amines and isocyanides, with tolerance to water and carboxylic acids.
Conclusions:
- Developed efficient and mild protocols for synthesizing highly functionalized α-amino amides and imides.
- The methodology offers a straightforward route to valuable chemical entities.
- Visible light photoredox catalysis provides a sustainable approach for C-H functionalization.
Related Concept Videos
01:26Photochemical Electrocyclic Reactions: Stereochemistry
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Selection Rules: Photochemical Activation
01:12Cycloaddition Reactions: MO Requirements for Photochemical Activation
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
01:26Thermal and Photochemical Electrocyclic Reactions: Overview
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
01:24Redox Reactions
Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...
01:27Redox Reactions
Redox reactions are vital biochemical processes that underpin energy metabolism in cells. These reactions involve the transfer of electrons between molecules, occurring in tandem as oxidation and reduction. Oxidation refers to the loss of electrons, while reduction denotes their gain. This coupling ensures the seamless flow of electrons through metabolic pathways. For example, in bacterial metabolism, glucose undergoes oxidation to carbon dioxide, while oxygen is simultaneously reduced to...
01:27Phase I Reactions: Reductive Reactions
Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...