741825

XPhos Pd G2

98%

• Synonym(s): 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
• Empirical Formula (Hill Notation): C₄₅H₅₉ClNPPd
• CAS Number: 1310584-14-5
• Molecular Weight: 786.80
• UNSPSC Code: 12161600
• PubChem Substance ID: 329765534
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 98%
• form: solid
• feature: generation 2
• reaction suitability: core: palladium; 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 2^nd 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.

For small scale and high throughput uses, product is also available as ChemBeads (927775)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable