Journal
ORGANIC LETTERS
Volume 24, Issue 2, Pages 597-601Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c04038
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Funding
- NIH [1S10 OD020022-1]
- Ruth L. Kirschstein NRSA fellowship J.A.B. (UWMadison) [F32 GM129909]
- NSF [CHE-1048642]
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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.
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.
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