Buchwald Phosphine Ligands for Cross Coupling

The impact of cross-coupling methodologies to form C-C bonds is paramount in organic synthesis.¹ Of these, Suzuki-Miyaura coupling is among the most powerful transformations available as it has broad scope and wide functional group tolerance.² To this end, notable advances have been made in the laboratories of Prof. Stephen Buchwald at MIT.

We offer a series of Buchwald Ligands successfully used in processes, including Suzuki-Miyaura coupling, amination, amidation, enolate arylation, Sonogashira coupling and C-O bond formation (Table 1). While each ligand has documented utility, application of dimethoxy-substituted ligand 1, S-Phos, leads to a Pd-catalyst system with unprecedented scope, reactivity, and stability for Suzuki-Miyaura coupling processes.³ Selected examples (Table 2) illustrate the success of this system with respect to aryl chloride substrates, the generation of truly hindered biaryls, and heteroaryl cross-couplings.

References: 1, 4-12
Product numbers: 638072, 638099, 638064, 638439, 638080, 638021

Triisopropyl-substituted ligand 2, X-Phos has key applications to Pd-catalyzed C-N bond formation.⁴ Table 3 gives examples that typify the expanded scope of this process utilizing X-Phos. X-Phos has also been successfully applied to Suzuki-Miyaura couplings with arene and vinyl sulfonates⁵ (Table 2), as well as Sonogashira coupling of alkynes⁶ (Table 4). 2-Di-t-butylphoshino-2’,4’,6’- triisopropyl ligand has been found to be a superior ligand for Pd-catalyzed coupling of phenols with aryl bromides and chlorides.⁷