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Site-Selective C-H Functionalization of (Hetero)Arenes via Transient, Non-Symmetric Iodanes
Stacy C Fosu1, Chido M Hambira2, Andrew D Chen1
1The Ohio State University, Department of Chemistry and Biochemistry, Columbus, OH 43210, United States.
Abstract:
A strategy for C-H functionalization of arenes and heteroarenes has been developed to allow site-selective incorporation of various anions, including Cl, Br, OMs, OTs, and OTf. This approach is enabled by in situ generation of reactive, non-symmetric iodanes by combining anions and bench-stable PhI(OAc)2. The utility of this mechanism is demonstrated via para-selective chlorination of medicinally relevant arenes, as well as site-selective C-H chlorination of heteroarenes. Spectroscopic, computational, and competition experiments describe the unique nature, reactivity, and selectivity of these transient, unsymmetrical iodanes.
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