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Cu-catalyzed fluorination of diaryliodonium salts with KF.

ABSTRACT: A mild Cu-catalyzed nucleophilic fluorination of unsymmetrical diaryliodonium salts with KF is described. This protocol preferentially fluorinates the smaller aromatic ligand on iodine(III). The reaction exhibits a broad substrate scope and proceeds with high chemoselectivity and functional group tolerance. DFT calculations implicate a Cu(I)/Cu(III) catalytic cycle.

SUBMITTER: Ichiishi N

PROVIDER: S-EPMC4096328 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Cu-catalyzed fluorination of diaryliodonium salts with KF.

Ichiishi Naoko N Canty Allan J AJ Yates Brian F BF Sanford Melanie S MS

Organic letters 20130924 19

A mild Cu-catalyzed nucleophilic fluorination of unsymmetrical diaryliodonium salts with KF is described. This protocol preferentially fluorinates the smaller aromatic ligand on iodine(III). The reaction exhibits a broad substrate scope and proceeds with high chemoselectivity and functional group tolerance. DFT calculations implicate a Cu(I)/Cu(III) catalytic cycle. ...[more]

PMID: 24063629

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