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Issue 15, 2018
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EvanPhos: a ligand for ppm level Pd-catalyzed Suzuki–Miyaura couplings in either organic solvent or water

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Abstract

A new biaryl phosphine-containing platform can be constructed in only two steps. It complexes Pd(OAc)2 forming a precursor of a very active catalyst useful for Suzuki–Miyaura cross-couplings of functionalized substrates. By a combination of pre-activation, used together with the uncommon solvent EtOAc, the resulting catalyst system is effective at loadings in the ppm (0.1–0.5 mol%) range with highly functionalized reaction partners. Similar reactions run in water containing nanomicelles are as fast or faster. The derived Pd-complexed pre-catalyst possesses extended bench stability. The resulting technology represents an attractive green synthetic advance in highly valued Suzuki–Miyaura couplings.

Graphical abstract: EvanPhos: a ligand for ppm level Pd-catalyzed Suzuki–Miyaura couplings in either organic solvent or water

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Supplementary files

Article information


Submitted
30 Apr 2018
Accepted
14 Jun 2018
First published
02 Jul 2018

Green Chem., 2018,20, 3436-3443
Article type
Communication
Author version available

EvanPhos: a ligand for ppm level Pd-catalyzed Suzuki–Miyaura couplings in either organic solvent or water

E. B. Landstrom, S. Handa, D. H. Aue, F. Gallou and B. H. Lipshutz, Green Chem., 2018, 20, 3436
DOI: 10.1039/C8GC01356J

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