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Buchwald 4th Generation Palladacycles

We Currently Offer 8 Products from this Newest Generation of Palladacycles

Strem is pleased to provide further advancement in Buchwald Palladacycle technology by offering a 4th generation as “N-methyl” analogs of the catalysts’ 2-aminobiphenyl moiety.  Whereas the 2nd and 3rd generation Buchwald precatalysts fostered significant advances in organic syntheses and produced high yields with a wide variety of substrates, they were based on the 2-aminobiphenyl ligand.  However, the primary amino group in the ligand can lead to synthetic limitations, especially in a pharmaceutical environment.

Upon activation of the catalyst, the 2-aminobiphenyl converts mainly into carbazole, a secondary amine that itself can serve as a substrate in the coupling reactions of amines with aryl halides.  This side reaction can consume valuable starting material and lead to complications in purification.  Buchwald 4th generation precatalysts based on N-methyl biphenyl will produce N-methylcarbazole upon activation, which cannot act as substrate in these types of reactions. Another drawback from 3rd generation precatalyst is remaining traces of 2-aminobiphenyl in the product. Aminobiphenyls have been associated with carcinogenicity (4-aminobiphenyl is a known carcinogen); therefore, its absence is desirable, especially in pharmaceutical syntheses.

Gen. 4 Buchwald Palladacycles

Products mentioned in this blog and related products:

46-0327: Methanesulfonato(2-dicyclohexylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II), min. 98% [XPhos Palladacycle Gen. 4], CAS # 1599466-81-5

46-0330: Methanesulfonato(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II) dichloromethane adduct, min. 98% [t-BuXphos Palladacycle Gen. 4], CAS # 1599466-89-3

46-0333: Methanesulfonato(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II), min. 98% [BrettPhos Palladacycle Gen. 4], CAS # 1599466-83-7

46-0379: Methanesulfonato(tricyclohexylphosphino)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II), 98% [PCy3 Palladacycle Gen. 4]

46-0380: Methanesulfonato(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II) dichloromethane adduct min. 98% [SPhos Palladacycle Gen. 4], CAS # 1599466-87-1

46-0385: Methanesulfonato(tri-t-butylphosphino)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II), 98% [P(t-Bu)3 Palladacycle Gen. 4], CAS # 1621274-11-0

46-0388: Methanesulfonato[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene](2'-methylamino-1,1'-biphenyl-2-yl)palladium(II), 98% [Xantphos Palladacycle Gen. 4]

46-0395: Methanesulfonato(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II), min. 98% [RuPhos Palladacycle Gen. 4], CAS # 1599466-85-9

 

Visit the below links to view additional details and products on our website:

Buchwald 4th Generation Palladacycles

Buchwald Precatalysts & Ligands

 

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