Challenging cross couplings, in water, aided by in situ iodination of (hetero)aromatic bromides

Palladium-catalyzed reactions that involve functionalized substrates are oftentimes problematic. Those involving aryl or heteroaryl bromides that are either resistant to, or inefficient in such couplings present challenges that are difficult to overcome and may require development of an entirely new...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2023-11, Vol.14 (46), p.13503-13507
Main Authors: Thomas, Rohan M., Obbard, David B., Lipshutz, Bruce H.
Format: Article
Language:English
Subjects:
Bromides
Chemical reactions
Chemistry
Couplings
Iodination
Palladium
Substrates
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Summary:Palladium-catalyzed reactions that involve functionalized substrates are oftentimes problematic. Those involving aryl or heteroaryl bromides that are either resistant to, or inefficient in such couplings present challenges that are difficult to overcome and may require development of an entirely new route, or worse, no opportunity to install the desired group using a standard coupling strategy. In this report, we describe a solution that allows for the in situ conversion of such bromo educts to transient iodide derivatives that can be made and used under environmentally responsible conditions, for subsequent reactions to highly functionalized, complex targets.
ISSN:2041-6520
2041-6539
DOI:10.1039/d3sc04199a