Issue 6, 2016

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
21 yan 2016
Accepted
18 fev 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
Creative Commons BY license

Chem. Sci., 2016,7, 3780-3784

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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