Abstract
Oxidative cleavage of alkenes leading to valuable carbonyl derivatives is a fundamental
transformation in synthetic chemistry. In particular, ozonolysis is the mainstream
method for the oxidative cleavage of alkenes that has been widely implemented in the
synthesis of natural products and pharmaceutically relevant compounds. However, due
to the toxicity and explosive nature of ozone, alternative approaches employing transition
metals and enzymes in the presence of oxygen and/or strong oxidants have been developed.
These protocols are often conducted under harsh reaction conditions that limit the
substrate scope. Photochemical approaches can provide milder and more practical alternatives
for this synthetically useful transformation. In this review, we outline recent visible-light-promoted
oxidative cleavage reactions that involve photocatalytic activation of oxygen via
electron transfer and energy transfer. Also, an emerging field featuring visible-light-promoted
oxidative cleavage under anaerobic conditions is discussed. The methods highlighted
in this review represent a transformative step toward more sustainable and efficient
strategies for the oxidative cleavage of alkenes.
1 Introduction
2 Photochemical Methods for Oxidative Cleavage of Alkenes under Aerobic Conditions
2.1 Transition-Metal-Catalyzed Oxidative Cleavage of Alkenes under Visible Light
2.2 Photopromoted Organocatalyzed Oxidative Cleavage of Alkenes
2.3 Oxidative Cleavage of Alkenes with Molecular Iodine under Visible Light
2.4 Polymer-Catalyzed Oxidative Cleavage under Visible Light Irradiation
2.5 Oxidative Cleavage via Direct Visible Light Excitation with Molecular Oxygen
3 Anaerobic Oxidative Cleavage of Alkenes under Visible Light
4 Conclusion
Key words
oxidative cleavage - alkenes - ozonolysis - nitroarenes - photochemistry - anaerobic
- visible light - aerobic
