An electrophotochemical ring-opening bromination of unstrained tert-cycloalkanols has been developed. This electrophotochemical method enables the oxidative transformation of cycloalkanols with 5-to 7membered rings into synthetically useful ω-bromoketones without the use of chemical oxidants or transition-metal catalysts. Alkoxy radical species would be key intermediates in the present transformation, which generate through homolysis of the O−Br bond in hypobromite intermediates under visible light irradiation.

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An oxidative C–N bond cleavage of cyclic amines has been developed under metal-free conditions, providing N-Cl-ω-amino acids in moderate to excellent yields. The reactions successfully proceed by using tetramethylammonium hypochlorite (TMAOCl) as an oxidant even on a gram scale. The Hofmann–Löffler–Freytag-type reaction of N-Cl-ω-amino acids to form cyclic amino acids are also demonstrated.