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Herein we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C-H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups such as -F, -Cl, -Br, -CH3, -Et, -iPr -OCH3 and -OCF3. It also provides regioselective access to the nitro derivatives of π-electron deficient heterocycles such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine via Baran's amination protocol.
This article was published in the following journal.
Name: Chemistry (Weinheim an der Bergstrasse, Germany)
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Any of three isomeric compounds (ortho-, meta-, and para-) containing a benzene ring with a methyl and amino group attached to it. They are suspected CARCINOGENS.
Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.
Includes ortho-, meta-, and para-nitrophenylgalactosides.
Compounds consisting of three benzene rings linked to each other in either ortho, meta or para positions and substituted with chlorine atoms.
Compounds consisting of benzene rings linked to each other in either ortho, meta or para positions. Permitted are any substitutions, but ring fusion to any of the benzene rings is not allowed.
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