Xantphos is an organophosphorus compound derived from the

heterocycle A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

xanthene Xanthene (9''H''-xanthene, 10''H''-9-oxaanthracene) is the organic compound with the formula CH2 6H4sub>2O. It is a yellow solid that is soluble in common organic solvents. Xanthene itself is an obscure compound, but many of its derivatives are us ...

. It is used as a bidentate

diphosphine Diphosphane, or diphosphine, is an inorganic compound with the chemical formula P2H4. This colourless liquid is one of several binary phosphorus hydrides. It is the impurity that typically causes samples of phosphine to ignite in air. Proper ...

ligand In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...

and is noteworthy for having a particularly wide

bite angle In coordination chemistry the bite angle is the ligand–metal–ligand bond angle of coordination complex containing a bidentate ligand. This geometric parameter is used to classify chelating ligands, including those in organometallic complexes ...

(108°). Such ligands are useful in the

hydroformylation Hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes from alkenes. This chemical reaction entails the net addition of a formyl group (CHO) and a hydrogen atom to a carbon-carbon d ...

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

s. Illustrative of its wide bite angle, it forms both cis and trans adducts of

platinum(II) chloride Platinum(II) chloride is the chemical compound Pt Cl2. It is an important precursor used in the preparation of other platinum compounds. It exists in two crystalline forms, but the main properties are somewhat similar: dark brown, insoluble in wa ...

. In the latter context, xantphos is classified as a trans-spanning ligand. A related bidentate ligand with a greater bite angle is spanphos. The ligand is prepared by double directed lithiation of 9,9-dimethylxanthene with

sec-butyllithium ''sec''-Butyllithium is an organometallic compound with the formula CH3CHLiCH2CH3, abbreviated ''sec''-BuLi or ''s''-BuLi. This chiral organolithium reagent is used as a source of ''sec''-butyl carbanion in organic synthesis.. Synthesis ''sec'' ...

followed by treatment with

chlorodiphenylphosphine Chlorodiphenylphosphine is an organophosphorus compound with the formula (C6H5)2PCl, abbreviated Ph2PCl. It is a colourless oily liquid with a pungent odor that is often described as being garlic-like and detectable even in the ppb range. It is u ...

.{{cite journal , author = Mirko Kranenburg, Yuri E. M. van der Burgt, Paul C. J. Kamer, Piet W. N. M. van Leeuwen, Kees Goubitz, and Jan Fraanje , title = New Diphosphine Ligands Based on Heterocyclic Aromatics Inducing Very High Regioselectivity in Rhodium-Catalyzed Hydroformylation: Effect of the Bite Angle , year = 1995 , journal =

Organometallics ''Organometallics'' is a biweekly journal published by the American Chemical Society. Its area of focus is organometallic and organometalloid chemistry. This peer-reviewed journal has an impact factor of 3.837 as reported by the 2021 Journal Cit ...

, volume = 14 , issue = 6, pages = 3081–3089 , doi = 10.1021/om00006a057, url = https://pure.uva.nl/ws/files/2969936/882_9954y.pdf

References

Diphosphines