Photoinduced Fe-catalyzed bromination and iodination of unstrained cyclic alcohols

We report a photoinduced iron catalysis for the efficient C-C bond cleavage and bromination or iodination of unstrained tertiary cycloalkanols with NBS/NIS. The reaction features good functional group tolerance and high yields under mild conditions and provides a powerful tool for the preparation of remote halogenated alkyl ketones. The products can be converted via nucleophilic substitution or cross-coupling to other valuable molecules, such as haloperidol, fluanisone, and azabuperone, demonstrating the synthetic value of this reaction.

Automated summary

This study presents a photoinduced iron catalysis that efficiently cleaves C-C bonds and brominates or iodinates unstrained tertiary cycloalkanols using NBS/NIS. The reaction demonstrates good functional group tolerance and high yields under mild conditions, providing a powerful tool for the synthesis of remote halogenated alkyl ketones. The resulting products can be further converted to valuable molecules through nucleophilic substitution or cross-coupling reactions.