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

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 ana...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2016-01, Vol.7 (6), p.378-3784
Main Authors: Jardim, Guilherme A. M, da Silva Júnior, Eufrânio N, Bower, John F
Format: Article
Language:English
Subjects:
Bonding
Carbon-carbon composites
Catalysis
Deactivation
Derivatives
Forming
Iodination
Rhodium
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Summary: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. Rh-catalyzed C-5 selective C-H iodination of naphthoquinones provides a gateway to previously inaccessible A-ring analogues. C-2 selective processes can be achieved under related conditions.
ISSN:2041-6520
2041-6539
DOI:10.1039/c6sc00302h