Bench-Stable Bicyclo[1.1.1]pentane Precursors for Photoredox Radical Coupling

Keywords

bicyclo[1.1.1]pentanes - photoredox - copper catalysis

Significance

The authors utilized N-hydroxyphthalimide (NHPI)-functionalized bicyclo[1.1.1]pentanes (BCPs) as radical coupling partners. An in situ generated silyl radical acted as the key halogen atom transfer (XAT) reagent to produce alkyl or aryl radicals from alkyl or aryl bromides.

 

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Comment

This methodology was carried out successfully on analogues containing drug-relevant structural motifs, showcasing potential application in a pharmaceutical setting. Aryl, heteroaryl, primary, secondary, and tertiary alkyl coupling partners were all tolerated, highlighting the broad functional group tolerance of this method.

 

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Publication History

Article published online:
23 June 2025