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XPhos

Not to be confused with Xantphos.

XPhos is a phosphine ligand derived from biphenyl. 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 amides. 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.

XPhos
Names
Preferred IUPAC name
Dicyclohexyl[2′,4′,6′-tris(propan-2-yl)[1,1′-biphenyl]-2-yl]phosphane
Other names
XPhos
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.123.428
UNII
  • InChI=1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3 N
    Key: UGOMMVLRQDMAQQ-UHFFFAOYSA-N N
  • InChI=1/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3
    Key: UGOMMVLRQDMAQQ-UHFFFAOYAR
  • P(c2ccccc2c1c(cc(cc1C(C)C)C(C)C)C(C)C)(C3CCCCC3)C4CCCCC4
Properties
C33H49P
Molar mass 476.72
Appearance colorless solid
Melting point 187 to 190 °C (369 to 374 °F; 460 to 463 K)
organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Nverify (what is YN ?)
Infobox references
  • One view of the molecule's structure.

  • Another view of the molecule's structure.

  1. Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. (2003). "Expanding Pd-Catalyzed C-N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions". J. Am. Chem. Soc. 125 (22): 6653–6655. doi:10.1021/ja035483w. PMID 12769573.
  2. Bruno, Nicholas C.; Tudge, Matthew T.; Buchwald, Stephen L. (2013-02-04). "Design and preparation of new palladium precatalysts for C–C and C–N cross-coupling reactions". Chemical Science. 4 (3): 916–920. doi:10.1039/C2SC20903A. ISSN 2041-6539. PMC3647481. PMID 23667737.
  3. Yang, Yang; Oldenhuis, Nathan J.; Buchwald, Stephen L. (2013). "Mild and General Conditions for Negishi Cross-Coupling Enabled by the Use of Palladacycle Precatalysts". Angew. Chem. Int. Ed. 52 (2): 615–619. doi:10.1002/anie.201207750. PMC3697109. PMID 23172689.
  4. Gelman, Dmitri; Buchwald, Stephen L. (2003). "Efficient Palladium-Catalyzed Coupling of Aryl Chlorides and Tosylates with Terminal Alkynes: Use of a Copper Cocatalyst Inhibits the Reaction". Angew. Chem. Int. Ed. 42 (48): 5993–5996. doi:10.1002/anie.200353015. PMID 14679552.
  5. Altman, R.A.; Fors, B.P.; Buchwald, S.L. (2007). "Pd-Catalyzed Amination Reactions of Aryl Halides Using Bulky Biarylmonophosphine Ligands". Nature Protocols. 2 (11): 2881–2887. doi:10.1038/nprot.2007.414. PMID 18007623.

XPhos
XPhos Language Watch Edit Not to be confused with Xantphos XPhos is a phosphine ligand derived from biphenyl 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 amides 1 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 2 3 4 The ligand itself also has convenient handling characteristics as a crystalline air stable solid 5 XPhos NamesPreferred IUPAC name Dicyclohexyl 2 4 6 tris propan 2 yl 1 1 biphenyl 2 yl phosphaneOther names XPhosIdentifiersCAS Number 564483 18 7 Y3D model JSmol Interactive imageChemSpider 9330902 NECHA InfoCard 100 123 428PubChem CID 11155794UNII R271FU23T8 YCompTox Dashboard EPA DTXSID50457126InChI InChI 1S C33H49P c1 23 2 26 21 30 24 3 4 33 31 22 26 25 5 6 29 19 13 14 20 32 29 34 27 15 9 7 10 16 27 28 17 11 8 12 18 28 h13 14 19 25 27 28H 7 12 15 18H2 1 6H3 NKey UGOMMVLRQDMAQQ UHFFFAOYSA N NInChI 1 C33H49P c1 23 2 26 21 30 24 3 4 33 31 22 26 25 5 6 29 19 13 14 20 32 29 34 27 15 9 7 10 16 27 28 17 11 8 12 18 28 h13 14 19 25 27 28H 7 12 15 18H2 1 6H3Key UGOMMVLRQDMAQQ UHFFFAOYARSMILES P c2ccccc2c1c cc cc1C C C C C C C C C C3CCCCC3 C4CCCCC4PropertiesChemical formula C33H49PMolar mass 476 72Appearance colorless solidMelting point 187 to 190 C 369 to 374 F 460 to 463 K Solubility in water organic solventsExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesStructure Edit One view of the molecule s structure Another view of the molecule s structure See also EditSPhos CPhos Buchwald Hartwig reactionReferences Edit Huang X Anderson K W Zim D Jiang L Klapars A Buchwald S L 2003 Expanding Pd Catalyzed C N Bond Forming Processes The First Amidation of Aryl Sulfonates Aqueous Amination and Complementarity with Cu Catalyzed Reactions J Am Chem Soc 125 22 6653 6655 doi 10 1021 ja035483w PMID 12769573 Bruno Nicholas C Tudge Matthew T Buchwald Stephen L 2013 02 04 Design and preparation of new palladium precatalysts for C C and C N cross coupling reactions Chemical Science 4 3 916 920 doi 10 1039 C2SC20903A ISSN 2041 6539 PMC 3647481 PMID 23667737 Yang Yang Oldenhuis Nathan J Buchwald Stephen L 2013 Mild and General Conditions for Negishi Cross Coupling Enabled by the Use of Palladacycle Precatalysts Angew Chem Int Ed 52 2 615 619 doi 10 1002 anie 201207750 PMC 3697109 PMID 23172689 Gelman Dmitri Buchwald Stephen L 2003 Efficient Palladium Catalyzed Coupling of Aryl Chlorides and Tosylates with Terminal Alkynes Use of a Copper Cocatalyst Inhibits the Reaction Angew Chem Int Ed 42 48 5993 5996 doi 10 1002 anie 200353015 PMID 14679552 Altman R A Fors B P Buchwald S L 2007 Pd Catalyzed Amination Reactions of Aryl Halides Using Bulky Biarylmonophosphine Ligands Nature Protocols 2 11 2881 2887 doi 10 1038 nprot 2007 414 PMID 18007623 Retrieved from https en wikipedia org w index php title XPhos amp oldid 1018162257, wikipedia, wiki, book,

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