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741825

XPhos Pd G2

98%, solid

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

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About This Item

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

XPhos Pd G2, 98%

Quality Segment

100

product line

Buchwald precatalyst Generation 2

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

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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