Herein,
we report a new photochemical method for C(sp3)–H
chlorination of amides which employs tert-butyl hypochlorite
as the chlorinating agent and a household compact
fluorescent lamp as the light source. The reaction proceeds via N-heterocyclic
carbene SIPr·HCl-promoted N–H chlorination and subsequent
photoinduced Hofmann–Löffler–Freytag chlorine
atom transfer. The latter process is facilitated by (diacetoxyiodo)benzene.
This protocol exhibits a broad scope and is suitable for site-selective
chlorination of methyl hydrogen as well as methylene and methine hydrogen.
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