753009

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: 1375325-64-6
• Molecular Weight: 720.62
• MDL number: MFCD20264897
• UNSPSC Code: 12161600
• PubChem Substance ID: 329766331
• NACRES: NA.22

Properties

• 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: 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

Description

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable