Ligated Pd-Catalyzed Aminations of Aryl/Heteroaryl Halides with Aliphatic Amines under Sustainable Aqueous Micellar Conditions

Abstract

Sustainable technology for constructing Pd-catalyzed C−N bonds involving aliphatic amines is reported. A catalytic system that relies on low levels of recyclable precious metal, a known and commercially available ligand, and a recyclable aqueous medium are combined, leading to a newly developed procedure. This new technology can be used in ocean water with equal effectiveness. Applications involving highly challenging reaction partners constituting late-stage functionalization are documented, as is a short but efficient synthesis of the drug naftopidil. Comparisons with existing aminations highlight the many advances being offered.

Micelles Enabled Nickel-Catalyzed P-Arylation of Aromatic Phosphine Oxide in Water Under Mild Conditions

“…New advances in chemical synthesis and catalysis are nowadays strongly linked to green and sustainable chemistry, and the choice of solvents and catalysts are the key factors in determining the environmental and economic impacts of a chemical process. , Micellar catalysis is an enabler for performing chemistry in water under very mild conditions, thus mimicking nature. − Lipshutz et al, − Handa et al, − Kobayashi et al, , and others , have contributed significantly over the last decades to advance the field of micellar catalysis, and nowadays, this technology has also been adopted by various pharmaceutical and agrochemical industries. − Although several crucial cross-couplings, such as C–C and C–N, have been reported under aqueous micellar conditions, mostly these reactions are dominated by using expensive Pd catalysts. − , …”