Cu-Catalyzed Site-Selective Benzylic Chlorination Enabling Net C-H Coupling with Oxidatively Sensitive Nucleophiles

Site-selective chlorination of benzylic C-H bonds is achieved using a (CuCl)-Cl-I/bis(oxazoline) catalyst with N-fluorobenzenesulfonimide as the oxidant and KCl as a chloride source. This method exhibits higher benzylic selectivity, relative to established chlorination protocols, and is compatible with diverse alkyl arenes. Sequential benzylic C-H chlorination/nucleophilic substitution affords C-O, C-S, and C-N coupling products with oxidatively sensitive coupling partners.

Automated summary

Site-selective chlorination of benzylic C-H bonds is achieved using a specific catalyst and oxidant, resulting in higher selectivity and compatibility with diverse alkyl arenes. Sequential benzylic C-H chlorination/nucleophilic substitution leads to coupling products with oxidatively sensitive partners.