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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.
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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.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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

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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.

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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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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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.

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Related Experiment Video

Updated: Aug 13, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Published on: June 20, 2014

Photocatalytic Late-Stage C-H Functionalization.

Peter Bellotti¹, Huan-Ming Huang², Teresa Faber¹

¹Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 36, 48149Münster, Germany.

Chemical Reviews

|January 24, 2023

Summary

Modern photocatalysis enables selective late-stage C-H functionalization using light. This review explores its application in drug discovery, comparing photocatalytic and traditional methods for novel synthetic strategies.

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Area of Science:

Organic Chemistry
Photocatalysis
Synthetic Methodology

Background:

Photocatalysis offers mild and selective reaction conditions.
Late-stage functionalization is crucial for drug development.
Traditional methods have limitations in selectivity and scope.

Purpose of the Study:

To review photocatalytic late-stage C-H functionalization strategies.
To compare photocatalysis with traditional ionic chemistry.
To highlight current advancements and future challenges in the field.

Main Methods:

Classification of photocatalytic C-H functionalization by targeted and newly formed bonds.
Analysis of mechanistic pathways in photocatalytic reactions.
Comparison of radical-based photocatalysis with ionic chemistry.

Main Results:

Photocatalysis provides complementary regio- and chemoselectivities.
Emerging strategies enable functionalization of drugs, agrochemicals, and natural products.
Key mechanistic scenarios are identified and compared.

Conclusions:

Photocatalytic late-stage C-H functionalization is a powerful tool for drug discovery.
Further research is needed to address current challenges and explore new directions.
This review provides a comprehensive overview for researchers in the field.