1310584-14-5

Basic information

• Product Name: XPhos Pd G2
• Synonyms: Chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-aMino-1,1'-biphenyl)]palladiuM(II);Chloro(2-dicyclohexylphosphin;Chloro(2-dicyclohexylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-aMino-1,1'-biphenyl-2-yl) palladiuM(II), Min. 98% [XPhos Palladacycle];(SP-4-4)-[2'-Amino[1,1'-biphenyl]-2-yl]chloro[dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine]palladium;XPhos Pd G2;2nd Generation XPhos Precatalyst;X-Phos aminobiphenyl palladium chloride precatalyst;Palladium-Xphos
• CAS NO: 1310584-14-5
• Molecular Formula: C₄₅H₅₉ClNPPd
• Molecular Weight: 785.795481
• Product Categories: Buchwald Ligands&Precatalysts;Buchwald Precatalysts Series;Pd
• Mol File: 1310584-14-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 202-210°C
• Appearance: white/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: XPhos Pd G2(CAS DataBase Reference)
• NIST Chemistry Reference: XPhos Pd G2(1310584-14-5)
• EPA Substance Registry System: XPhos Pd G2(1310584-14-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 1310584-14-5(Hazardous Substances Data)

Usage

Description

XPhos Pd G2, also known as a bulky monodentate biaryl ligand, is a second-generation preformed catalyst developed by Buchwald. It is characterized by its rapid reductive elimination, which leads to the formation of a reactive, monoligated Pd(0) species. This unique property makes XPhos Pd G2 a highly effective catalyst in various chemical reactions.

Uses

Used in Chemical Synthesis:
XPhos Pd G2 is used as a catalyst for chemical reactions, specifically in the following applications:
1. Palladium-catalyzed Suzuki-Miyaura coupling reactions of potassium organotrifluoroborates and sulfamates. This application is crucial for the formation of carbon-carbon bonds, which are essential in the synthesis of various organic compounds.
2. Suzuki-Miyaura cross-coupling reactions of sensitive aryl and heteroarylboronic acids. XPhos Pd G2 plays a vital role in facilitating these reactions, which are important for the synthesis of complex organic molecules with potential applications in pharmaceuticals, agrochemicals, and materials science.
3. Synthesis of potassium Boc-protected secondary aminomethyltrifluoroborates, via Suzuki-Miyaura cross-coupling reaction. This application highlights the versatility of XPhos Pd G2 in catalyzing reactions involving the formation of carbon-nitrogen bonds, which are crucial for the synthesis of various biologically active compounds.

Reaction

Palladium precatalyst for Suzuki-Miyaura coupling reactions.

Synthetic route

palladium diacetate (3375-31-3) + 2-phenylaniline (90-41-5) + lithium chloride + XPhos (564483-18-7) → (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)) (1310584-14-5)

Conditions	Yield
In toluene NH2C6H4C6H5 reacted with Pd salt in toluene at 60°C, reacted withLiCl in acetone at room temp., reacted with (C6H11)2PC6H4C6H2(CH(CH3)2) 3 at room temp.;	83%

Upstream product

• 3375-31-3 palladium diacetate 
• 90-41-5 2-phenylaniline 
• 564483-18-7 XPhos 

Relevant articles and documents

A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids

Boronic acids which quickly deboronate under basic conditions, such as polyfluorophenylboronic acid and five-membered 2-heteroaromatic boronic acids, are especially challenging coupling partners for Suzuki-Miyaura reactions. Nevertheless, being able to use these substrates is highly desirable for a number of applications. Having found that monodentate biarylphosphine ligands can promote these coupling processes, we developed a precatalyst that forms the catalytically active species under conditions where boronic acid decomposition is slow. With this precatalyst, Suzuki-Miyaura reactions of a wide range of (hetero)aryl chlorides, bromides, and triflates with polyfluorophenyl, 2-furan, 2-thiophene, and 2-pyrroleboronic acids and their analogues proceed at room temperature or 40 °C in short reaction times to give the desired products in excellent yields.