EMAIL THIS PAGE TO A FRIEND
741825 Sigma-Aldrich

XPhos Pd G2

Synonym: 2nd Generation XPhos Precatalyst, Chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II), X-Phos aminobiphenyl palladium chloride precatalyst, XPhos-Pd-G2

  • CAS Number 1310584-14-5

  • Empirical Formula (Hill Notation) C45H59ClNPPd

  • Molecular Weight 786.80

  •  PubChem Substance ID 329765534

  •  NACRES NA.22

Purchase

Properties

Related Categories Buchwald 2nd Generation Palladacycles, Buchwald Ligands and Complexes, Catalysis and Inorganic Chemistry, Chemical Synthesis, Cross-Coupling,
Quality Level   100
reaction suitability   reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reaction type: Heck Reaction
  reaction type: Hiyama Coupling
  reaction type: Negishi Coupling
  reaction type: Sonogashira Coupling
  reaction type: Stille Coupling
  reaction type: Suzuki-Miyaura Coupling
  reagent type: catalyst
reaction type: Cross Couplings
mp   202-210 °C
functional group   phosphine
SMILES string   Nc1ccccc1-c2ccccc2[Pd]Cl.Nc3ccccc3-c4ccccc4[Pd]Cl.CC(C)c5cc(C(C)C)c(-c6cccc(c6)P(C7CCCCC7)C8CCCCC8)c(c5)C(C)C.CC(C)c9cc(C(C)C)c(c(c9)C(C)C)-c%10ccccc%10P(C%11CCCCC%11)C%12CCCCC%12
InChI   1S/2C33H49P.2C12H10N.2ClH.2Pd/c1-23(2)27-21-31(24(3)4)33(32(22-27)25(5)6)26-14-13-19-30(20-26)34(28-15-9-7-10-16-28)29-17-11-8-12-18-29;1-23(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;2*13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;;;;/h13-14,19-25,28-29H,7-12,15-18H2,1-6H3;13-14,19-25,27-28H,7-12,15-18H2,1-6H3;2*1-6,8-9H,13H2;2*1H;;/q;;;;;;2*+1/p-2
InChI key   HMRJFNBZAWHTGN-UHFFFAOYSA-L

Description

General description

XPhos Pd G2 is a bulky monodentate biaryl ligand. It is a Buchwald′s 2nd generation preformed catalyst. It undergoes rapid reductive elimination to form a reactive, monoligated Pd(0) species.

Application

2nd Generation Buchwald Precatalysts

• Widely used for Suzuki-Miyaura cross-coupling reactions

XPhos Pd G2 was employed as catalyst in the following reactions:
• Palladium-catalyzed Suzuki-Miyaura coupling reactions of potassium organotrifluoroborates and sulfamates.
• Suzuki-Miyaura cross-coupling reactions of sensitive aryl and heteroarylboronic acids.
• Synthesis of potassium Boc-protected secondary aminomethyltrifluoroborates, via Suzuki-Miyaura cross-coupling reaction.

Packaging

1, 5, 10, 25, 100, 500 g in glass bottle

250 mg in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number

Certificate of Origin (COO)

Please Enter a Lot Number

Catalysts
Protocols & Articles

Articles

A New Palladium Precatalyst Allows for the Fast Suzuki-Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids

A method for the Pd-catalyzed coupling of 2-aminothiazole derivatives with aryl bromides and triflates is described. Significantly, for this class of nucleophiles, the coupling exhibits a broad subst...
Keywords: Catalysis, Chromatography

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes, and aryl or vinyl halides (or triflates) to afford substituted alkenes.1,2 It is a useful carbon–carbon bond form...
Keywords: Asymmetric synthesis, Cancer, Catalysis, Coupling reactions, Cross couplings, Heck Reaction, Herbicides, Ligands, Organic synthesis, Solvents

Pd-Catalyzed Alkynylation of 2-Chloroacetates and 2-Chloroacetamides with Potassium Alkynyltrifluoroborates

A practical method for palladium-catalyzed cyanation of aryl halides using Pd/C is described. The new method can be applied to a variety of aryl bromide and active aryl chloride substrates to effect ...
Keywords: Catalysis, Chromatography, High performance liquid chromatography

Stephen Buchwald Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Stephen Buchwald Group – Professor Product Portal
Keywords: Aminations, Asymmetric catalysis, Asymmetric synthesis, Catalysis, Coupling reactions, Cross couplings, Fluorinations, Ligands, Solvents, transformation

Related Content

Buchwald Precatalysts and Ligand Guide

Dialkylbiaryl phospine ligands, and the precatalysts derived from them, are commonly referred to as Buchwald Precatalysts and Ligands. These reagents have developed into a highly valuable class of co...
Keywords: Catalysis, Ligands

Peer-Reviewed Papers
15

References

Related Products

related product

Product #

Description

Add to Cart

903728 DavePhos Pd G2

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?