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GPhos: A New Exciting Buchwald Ligand
15-3035 is a new member of the Buchwald ligands family that bears great promise in the organic synthesis field
Strem is pleased to announce the introduction of GPhos as the newest member of our Buchwald ligand family.
GPhos, 15-3035
During the last 20-25 years, Buchwald ligands have had a profound influence in synthetic chemistry, especially in drug discovery of the pharmaceutical industry due to their unique ability to enhance palladium catalyzed cross coupling reactions.
We currently offer ~30 of these phosphines developed by the Buchwald working group at MIT.
All these ligands have the 2-phosphino-biphenyl moiety as a common scaffold. Derived from this framework, all of them have different substituents on all possible positions, providing the ability to fine tune steric bulk and electronic properties.
The most prominent feature of the new GPhos ligand is its tert-Butoxy moiety adjacent to the Dicyclohexyl-phosphine function. This provides ample steric bulk next to the phosphorus donor atom and directing electron density into the upper ring.
Strem is known for offering one of the largest varieties of phosphorous compounds worldwide in our catalog for research scientists. An important subset of these compounds constitute the Buchwald ligands and their pre-catalysts. In these pre-catalysts, ligands and palladium are married together in well-defined air stable molecules that can be conveniently used without gloveboxes on the bench.
GPhos is a novel mono-phosphine Buchwald ligand that supports such a catalyst possessing improved stability. The GPhos-derived catalyst exhibits improved performance as well for room temperature C–N cross coupling reactions between a broad scope of primary amines and aryl halides.1 The ligand is designed to promote C–N cross coupling across a wide range of substrate classes with low catalyst loadings. It shows an improved relative rate of productive catalysis versus catalyst deactivation compared to previous catalysts. The GPhos-supported catalyst displays better reactivity than previous catalysts both under ambient conditions and at elevated temperatures. Its use allows for the coupling of a variety of primary amine and aniline nucleophiles, including (1) unhindered, (2) five-membered-ring N-heterocycle-containing, and (3) α-tertiary primary amines. Each of which previously required a different catalyst to achieve optimal results. The GPhos-supported catalyst is also well suited for coupling electron-deficient anilines as well as N-heterocycle-containing aryl halides and amines.
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Featured Product
15-3035 (3-(Tert-butoxy)-2',6'-diisopropyl-6-methoxy-[1,1'-biphenyl]-2-yl)dicyclohexylphosphane GPhos, 98% (2489243-29-8)
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