Site Selective Chlorination of C(sp3)-H Bonds Suitable for Late-Stage Functionalization.

We report a method for the highly selective chlorination of tertiary and benzylic C( sp 3 )-H bonds to produce the corresponding chlorides, generally in high yields. The reaction occurs with a mixture of an azidoiodinane, which generates a selective H-atom abstractor under mild conditions, and a readily-accessible and inexpensive copper(II) chloride complex, which efficiently transfers a chlorine atom. The reaction's exceptional functional group tolerance is demonstrated by the chlorination of >30 diversely functionalized substrates and the late-stage chlorination of a dozen derivatives of natural products and active pharmaceutical ingredients.
PMID: 33480134 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - January 21, 2021 Category: Chemistry Authors: Hartwig JF, Fawcett A, Keller MJ, Herrera Z Tags: Angew Chem Int Ed Engl Source Type: research