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 1 2016
Accepted
18 2 2016
First published
02 3 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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