XPhos is a

phosphine ligand A metal-phosphine complex is a In coordination complex containing one or more phosphine ligands. Almost always, the phosphine is an organophosphine of the type R3P (R = alkyl, aryl). Metal phosphine complexes are useful in homogeneous catalysis. P ...

derived from

biphenyl Biphenyl (also known as diphenyl, phenylbenzene, 1,1′-biphenyl, lemonene or BP) is an organic compound that forms colorless crystals. Particularly in older literature, compounds containing the functional group consisting of biphenyl less one ...

. Its palladium complexes exhibit high activity for Buchwald-Hartwig amination reactions involving aryl chlorides and aryl tosylates. Both palladium and copper complexes of the compound exhibit high activity for the coupling of aryl halides and aryl tosylates with various

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...

s. It is also an efficient ligand for several commonly used C–C bond-forming cross-coupling reactions, including the Negishi, Suzuki, and the copper-free Sonogashira coupling reactions. It is especially efficient and general when employed as a ( 2-aminobiphenyl)-cyclometalated palladium mesylate precatalyst complex (Buchwald's third generation precatalyst system), XPhos-G3-Pd, which is commercially available and stable to bench storage. The ligand itself also has convenient handling characteristics as a crystalline, air-stable solid.{{cite journal , author1=Altman, R.A. , author2=Fors, B.P. , author3=Buchwald, S.L. , title = Pd-Catalyzed Amination Reactions of Aryl Halides Using Bulky Biarylmonophosphine Ligands , year = 2007 , journal =

Nature Protocols ''Nature Protocols'', published by the Nature Publishing Group, is an on-line scientific journal publishing methods in a recipe-style format. The journal was launched in June 2006 and the content includes both classical methods and cutting-edge te ...

, volume = 2 , issue = 11, pages = 2881–2887 , doi = 10.1038/nprot.2007.414 , pmid = 18007623

Structure

Image:XPhos.PNG, One view of the molecule's structure. Image:XPhos2.PNG, Another view of the molecule's structure.

References

Tertiary phosphines

Structure

See also

References