Merck
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753009

Sigma-Aldrich

SPhos Pd G2

Synonym(s):
2nd Generation SPhos Precatalyst, Chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II), SPhos-Pd-G2
Empirical Formula (Hill Notation):
C38H45ClNO2PPd
CAS Number:
Molecular Weight:
720.62
MDL number:
PubChem Substance ID:

form

solid

Quality Level

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

218 °C (dec.)

functional group

phosphine

SMILES string

COC1=CC=CC(OC)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2.NC5=C(C6=C([Pd]Cl)C=CC=C6)C=CC=C5

InChI

1S/C26H35O2P.C12H10N.ClH.Pd/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;;/h9-11,16-21H,3-8,12-15H2,1-2H3;1-6,8-9H,13H2;1H;/q;;;+1/p-1

InChI key

NOMWEFBAPVZIIP-UHFFFAOYSA-M

General description

SPhos Pd G2 is a second generation (G2) precatalyst in which phenethylamine based backbone of the (G1) complex is substituted with a biphenyl-based ligand. This improvement on the previous generation allows creating the active palladium species at room temperature with weak phosphate or carbonate bases. The catalyst proves remarkably adept at achieving a variety of Suzuki-Miyaura couplings among other cross-coupling reactions.

Application

Application in Suzuki-Miyaura coupling:
  • Self-arylation of 1-alkyl-3-bromo-2-phenyl-2,1-borazaronaphthalenes to form 2,1-borazaronaphthols.
  • Suzuki–Miyaura coupling of [Ru(bpy)2]+ with 4-carboxyphenylboronic acid.
  • Suzuki–Miyaura coupling of β-borylated porphyrins with 2-iodoaniline.

Packaging

250 mg in glass bottle
1, 5 g in glass bottle

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

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Certificate of Origin

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