Issue 12, 2019

ppm Pd-catalyzed, Cu-free Sonogashira couplings in water using commercially available catalyst precursors

Abstract

A new catalyst that derives from commercially available precursors for copper-free, Pd-catalyzed Sonogashira reactions at the sustainable ppm level of precious metal palladium under mild aqueous micellar conditions has been developed. Both the palladium pre-catalyst and ligand are commercially available, bench stable, and highly cost-effective. The catalyst is applicable to both aryl- and heteroaryl-bromides as educts. A wide range of functional groups are tolerated and the aqueous reaction medium can be recycled. An application to a key intermediate associated with an active pharmaceutical ingredient (ponatinib) is discussed.

Graphical abstract: ppm Pd-catalyzed, Cu-free Sonogashira couplings in water using commercially available catalyst precursors

Supplementary files

Article information

Article type
Edge Article
Submitted
17 dek 2018
Accepted
27 yan 2019
First published
31 yan 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 3481-3485

ppm Pd-catalyzed, Cu-free Sonogashira couplings in water using commercially available catalyst precursors

B. Jin, F. Gallou, J. Reilly and B. H. Lipshutz, Chem. Sci., 2019, 10, 3481 DOI: 10.1039/C8SC05618H

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