Buchwald Precatalysts and Ligands

Dialkylbiaryl phospine ligands, and the precatalysts derived from them, are commonly referred to as Buchwald Precatalysts and Ligands. These reagents have developed into a highly valuable class of compounds for palladium catalysis and can now be used for a broad range of reactions. This brochure is designed to show the common uses and advantages of these powerful, and now commercially available, Buchwald Precatalysts and Ligands.

Buchwald Precatalysts

Buchwald Precatalysts are highly active for a range of Pd-catalyzed reactions. These bench-stable complexes can be activated under mildly basic conditions and provide a number of unique advantages over traditional palladium catalysts in terms of both activity and stability.

Figure 1. Different Pd Sources and Different Methods of Activation in C-N Cross-Coupling Reactions

Buchwald Ligands

Figure 2. Structural Features of Dialkylbiaryl Phosphine Ligands

Precatalysts

Product	Structure	Common Name	Application for Pd Catalysis
704954		XPhos Palladacycle	α-Arylation of aldehydes Buchwald-Hartwig amination
708739		tBuXPhos Palladacycle	α-Arylation of acetate esters Buchwald-Hartwig amination
704946		SPhos Palladacycle	Buchwald-Hartwig amination
707589		RuPhos Palladacycle	Buchwald–Hartwig amination
718750		BrettPhos Palladacycle	Buchwald–Hartwig amination
741825 New		2nd Generation XPhos Palladacycle	Suzuki coupling Low temperature Buchwald–Hartwig amination
753009 New		2nd Generation SPhos Palladacycle	Low temperature Buchwald–Hartwig amination
753246 Coming Soon		2nd Generation RuPhos Palladacycle	Low temperature Buchwald–Hartwig amination

Ligands

Product	Structure	Common Name	Application for Pd Catalysis
638099		Cyclohexyl JohnPhos	Suzuki coupling Negishi coupling Hiyama coupling Methylation of aryl halides α-Arylation of ketones Buchwald-Hartwig amination C-B bond formation Oxidation of alcohols to ketones
638021		DavePhos	Suzuki coupling Kumada-Corriu coupling α-Arylation of ketones Buchwald-Hartwig amination Rh catalyzed hydroamination
638064		XPhos	Suzuki coupling Sonogashira coupling Hiyama coupling Stille coupling Carbonyl enolate coupling Buchwald-Hartwig amination
638072		SPhos	Suzuki coupling Kumada-Corriu coupling Negishi coupling Buchwald-Hartwig amination
695262		MePhos	Suzuki coupling α-Arylation of ketones Buchwald-Hartwig amination
663131		RuPhos	Suzuki coupling Negishi coupling α-Arylation reaction of oxindoles Buchwald-Hartwig amination
718742		BrettPhos	Buchwald-Hartwig amination Trifluoromethylation of aryl chlorides
677280		SSPhos	Suzuki coupling Rh-catalyzed 1, 2-addition of arylboronic acids to aldehydes and ketones
695882		PhDavePhos	α-Arylation of α-amino acid esters Heteroarene benzylation Buchwald-Hartwig amination
638080		tBuXPhos	α-Arylation of tetramic acids Decarboxylative coupling of aromatic acids and aryl iodides Carboxylation of aryl bromides with CO2 Buchwald-Hartwig amination Buchwald-Hartwig C-O coupling
638439		JohnPhos	Suzuki coupling Heck coupling Buchwald-Hartwig amination Buchwald-Hartwig C-O coupling C-Si bond formation
675938		Tetramethyl di-tBuXPhos	Coversion of aryl halides to phenols Buchwald-Hartwig amination Buchwald-Hartwig C-O coupling
695211		tBuMePhos	α-Arylation of ketones Buchwald-Hartwig C-O coupling Formate reduction of N-heterocyclic allylic acetates
730998		tBuBrettPhos	Buchwald-Hartwig amination C-F bond formation O-arylation of ethyl acetohydroximate Conversion of aryl and vinyl triflates to bromides and chlorides Conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics
695874		tBuDavePhos	α-Arylation of esters Buchwald-Hartwig C-O coupling Coupling of ammonia with aryl halides C-Si bond formation
731013		JackiePhos	N-arylation of secondary amides