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Issue 6, 2016
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Overcoming naphthoquinone deactivation: rhodium-catalyzed C-5 selective C–H iodination as a gateway to functionalized derivatives

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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.

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

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Supplementary files

Article information


Submitted
21 Jan 2016
Accepted
18 Feb 2016
First published
02 Mar 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 3780-3784
Article type
Edge Article

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

G. A. M. Jardim, E. N. da Silva Júnior and J. F. Bower, Chem. Sci., 2016, 7, 3780
DOI: 10.1039/C6SC00302H

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