Deconstructive diversification through C-C single bond cleavage

Deconstructive functionalization through C-C bond cleavage can generate structures with modified carbon skeletons, which are challenging or even inaccessible to achieve otherwise. The highly desired transformations through C-C single bond cleavage are underexplored. Herein, we report a general procedure to produce halides from readily accessible alkyl alcohols through C-C single bond fragmentation. Catalyzed with iron chloride under visible light, this reaction performed efficiently to produce primary, secondary, and tertiary alkyl halides bearing various functional groups. The resulting halides are valuable synthons for versatile modifications. More importantly, because alcohol can be simply prepared from other functional groups including ester, aldehyde, ketone, alkene, etc., this method enabled a broadly useful C-C bond functionalization beyond using alcohol as the precursor through a two-step procedure. Through C-C single bond cleavage, the method establishes a general platform towards a highly valuable pool of unique synthons, which includes chiral fragments from abundant and inexpensive natural products.