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753009

Sigma-Aldrich

SPhos Pd G2

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

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

Certificate of Origin

Accessing 2, 1-Borazaronaphthols: Self-Arylation of 1-Alkyl-2-aryl-3-bromo-2, 1-borazaronaphthalenes
Molander, Gary A and Wisniewski, Steven R
The Journal of Organic Chemistry, 79(17), 8339-8347 (2014)
Pictet-Spengler Synthesis of Quinoline-Fused Porphyrins and Phenanthroline-Fused Diporphyrins
Gao K, et al.
Angewandte Chemie (International Edition in English), 55(42), 13038-13042 (2016)
Modular synthesis of simple cycloruthenated complexes with state-of-the-art performance in p-type DSCs
Brunner F, et al.
Journal of Material Chemistry C, 4(41), 9823-9833 (2016)

Articles

Scale-Up Guide: Suzuki-Miyaura Cross-Coupling Reaction

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form.

KitAlysis™ Suzuki-Miyaura Cross-Coupling Reaction Screening Kit

Multiple tools have been created to ensure your success with kit set up. Start with the more detailed guide to ensure you are comfortable with all of the steps before using the quick guides on the excel worksheet. Remember that while the technique is new, it is still organic chemistry and so the steps will seem easy once you try just one kit. It is just a new way of approaching something you are already very good at.

KitAlysis High-Throughput Palladium Precatalyst Cross-Coupling Reaction Screening Kit

Materials Included in your KITALYSIS-24PD-2PK High-Throughput Screening Kit

Scale-Up Guide: Buchwald-Hartwig Amination Reaction

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive to air. To best enable scale-up success, the use of standard Schlenk technique is recommended.

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