753009

SPhos Pd G2

• Synonyme(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
• Formule empirique (notation de Hill): C₃₈H₄₅ClNO₂PPd
• Numéro CAS: 1375325-64-6
• Poids moléculaire : 720.62
• Numéro MDL: MFCD20264897
• Code UNSPSC : 12161600
• ID de substance PubChem : 329766331
• Nomenclature NACRES : NA.22

Propriétés

• Forme: solid
• Caractéristiques: generation 2
• Pertinence de la réaction: core: palladium; reagent type: catalyst; reaction type: Cross Couplings
• Capacité de réaction: 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
• Pf: 218 °C (dec.)
• Groupe fonctionnel: phosphine
• Chaîne SMILES: 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
• Clé InChI: NOMWEFBAPVZIIP-UHFFFAOYSA-M

Description

Description générale

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.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable