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Issue 38, 2019
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A new, substituted palladacycle for ppm level Pd-catalyzed Suzuki–Miyaura cross couplings in water

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Abstract

A newly engineered palladacycle that contains substituents on the biphenyl rings along with the ligand HandaPhos is especially well-matched to an aqueous micellar medium, enabling valued Suzuki–Miyaura couplings to be run not only in water under mild conditions, but at 300 ppm of Pd catalyst. This general methodology has been applied to several targets in the pharmaceutical area. Multiple recyclings of the aqueous reaction mixture involving both the same as well as different coupling partners is demonstrated. Low temperature microscopy (cryo-TEM) indicates the nature and size of the particles acting as nanoreactors. Importantly, given the low loadings of Pd invested per reaction, ICP-MS analyses of residual palladium in the products shows levels to be expected that are well within FDA allowable limits.

Graphical abstract: A new, substituted palladacycle for ppm level Pd-catalyzed Suzuki–Miyaura cross couplings in water

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Supplementary files

Article information


Submitted
23 May 2019
Accepted
02 Aug 2019
First published
06 Aug 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 8825-8831
Article type
Edge Article

A new, substituted palladacycle for ppm level Pd-catalyzed Suzuki–Miyaura cross couplings in water

B. S. Takale, R. R. Thakore, S. Handa, F. Gallou, J. Reilly and B. H. Lipshutz, Chem. Sci., 2019, 10, 8825
DOI: 10.1039/C9SC02528F

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