SYNTHESIS Best Paper Award 2018: A General Protocol for Radical Anion [3+2] cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis
Tehshik Yoon highlights his award-winning paper on the tandem-catalyzed radical anion [3+2] cycloaddition.
The award-winning article describes general protocol for radical anion [3+2] cycloaddition enabled by tandem Lewis acid photoredox catalysis. The Diels–Alder cycloaddition is often referred to as the “most powerful organic reaction.” Whether or not this assessment is still true in 2019, it is certainly the case that a large variety of six-membered carbocycles can be synthesized in a straightforward manner using Diels–Alder cycloaddition chemistry. Five-membered carbocycles, on the other hand, are comparatively more difficult to assemble. The purpose of the study reported in the paper of Tehshik Yoon was to explore the scope of a formal [3+2] cycloaddition that his co-workers had discovered. The reaction involves a novel radical mechanism, which they thought might allow a broad range of reaction partners to participate in the cycloaddition. The group’s hope was to demonstrate that this new method could start bridging the gap between the capabilities of existing [3+2] cycloaddition methods and reactions as powerful as the Diels–Alder reaction.
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