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Photochemical Electrocyclic Reactions: Stereochemistry

Photochemical 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

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Cycloaddition 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.

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal 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.

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...

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Updated: Sep 15, 2025

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Homoleptic copper(I)-bisphosphine complexes as photoredox catalysts.

Priya Saha¹, Ryunosuke Tomita², Takao Tsuneda¹

¹Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Japan. dcyhuang@icredd.hokudai.ac.jp.

Dalton Transactions (Cambridge, England : 2003)

|July 17, 2025

Summary

This study explores homoleptic copper-bisphosphine (CuP4) complexes in photoredox catalysis. These complexes show promise in organic synthesis, offering new avenues for designing advanced copper photocatalysts.

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

Area of Science:

Organic Chemistry
Photocatalysis
Coordination Chemistry

Background:

Copper photoredox catalysis is a key tool in organic synthesis.
Tetracoordinate copper complexes, particularly CuN4 and CuN2P2, are widely used.
Homoleptic copper-bisphosphine (CuP4) complexes are underexplored.

Purpose of the Study:

To systematically investigate homoleptic copper-bisphosphine (CuP4) complexes.
To characterize their photophysical and electrochemical properties.
To evaluate their potential in photocatalytic applications.

Main Methods:

Synthesis of representative CuP4 complexes.
Characterization of photophysical and electrochemical properties.
Testing photocatalytic activity in coupling reactions.

Main Results:

CuP4 complexes were successfully synthesized and characterized.
Their photophysical and electrochemical properties were elucidated.
Demonstrated photocatalytic activity in coupling reactions.

Conclusions:

Homoleptic copper-bisphosphine (CuP4) complexes are viable photocatalysts.
This study provides foundational data for future ligand design.
Highlights potential for developing novel, highly active copper-based photocatalysts.