Overcoming naphthoquinone deactivation: rhodium-catalyzed C-5 selective C-H iodination as a gateway to functionalized derivatives

Guilherme Jardim, Eufranio da Silva Junior, John Bower

Research output: Contribution to journalArticle (Academic Journal)peer-review

31 Citations (Scopus)
441 Downloads (Pure)

Abstract

We report a Rh-catalyzed method for the C-5 selective C–H iodination of naphthoquinones and show that complementary C-2 selective processes can be achieved under related conditions. C–C bond forming derivatizations of the C-5 iodinated products provide a gateway to previously inaccessible A-ring analogues. The present study encompasses the first catalytic directed ortho-functionalizations of simple (non-bias) naphthoquinones. The strategic considerations outlined here are likely to be applicable to C–H functionalizations of other weakly coordinating and/or redox sensitive substrates.
Original languageEnglish
Pages (from-to)3780-3784
Number of pages5
JournalChemical Science
Volume7
Issue number6
Early online date2 Mar 2016
DOIs
Publication statusPublished - 1 Jun 2016

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