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Site-Selective C-H Functionalization of (Hetero)Arenes via Transient, Non-Symmetric Iodanes.

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.

SUBMITTER: Fosu SC 

PROVIDER: S-EPMC6481961 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Site-Selective C-H Functionalization of (Hetero)Arenes via Transient, Non-Symmetric Iodanes.

Fosu Stacy C SC   Hambira Chido M CM   Chen Andrew D AD   Fuchs James R JR   Nagib David A DA  

Chem 20181213 2

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 <i>in situ</i> generation of reactive, non-symmetric iodanes by combining anions and bench-stable PhI(OAc)<sub>2</sub>. The utility of this mechanism is demonstrated via <i>para</i>-selective chlorination of medicinally relevant arenes, as well as site-selective C-H chlorination of heteroarenes  ...[more]

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