Copper(I) Oxide/N,N′‐Bis[(2‐furyl)methyl]oxalamide‐Catalyzed Coupling of (Hetero)aryl Halides and Nitrogen Heterocycles at Low Catalytic Loading

Abstract

An easily preparedo xalic diamide is ap owerful ligandf or the copper-catalyzed coupling of aryl halides with nitrogen heterocycles.O nly 1-2mol% each of copper(I) oxide and N,N'-bis[(2-furyl)methyl]oxalamide (BFMO) are needed to form N-arylation productsu nder mild conditions.M ore than 10 different typeso fn itrogen heterocycles are compatible with these conditions,t hereby givingt he corresponding N-arylation products.

Identification of an Oxalamide Ligand for Copper‐Catalyzed C−O Couplings from a Pharmaceutical Compound Library

“…Two initial hits gave ≥25 % conversion to ether 3 a , which guided another iteration of more focused substructure searches based on the 1,2‐ethylenediamine and 2‐(aminomethyl)thiophene scaffolds. The subsequent round of screening led to the identification of symmetrical oxalamide ligand 4 e as a promising lead. Further optimization of 4 e through rational design and structure‐activity studies led to the determination that the thiophene analogue 4 i was most effective for this coupling .…”

“…Further optimization of 4 e through rational design and structure‐activity studies led to the determination that the thiophene analogue 4 i was most effective for this coupling . Although oxalamides have been demonstrated to be viable ligands for a variety of Cu‐catalyzed transformations, these results highlight how the molecular diversity present in a pharmaceutical compound library can lead to the identification of functional ligand structures and inspire ligand design …”

Electrochemical Regioselective Bromination of Electron-Rich Aromatic Rings Using n Bu4NBr

“…The 1 H and 13 C spectra data matched with values reported in the literature. 10 Colorless oil, 69 % yield.…”

Ausgewählte Kupfer‐katalysierte Reaktionen für die Bildung von C‐N‐, C‐O‐, C‐S‐ und C‐C‐Bindungen

“…Vor kurzem haben Ma und Mitarbeiter gefunden, dass das leicht herstellbare Oxalsäurediamid L29 (BFMO) ein guter Ligand für die Cu‐katalysierte Kupplung von (Hetero)Arylhalogeniden mit N‐Heterocyclen ist (Schema ) . Nur 1–2 Mol‐% Cu 2 O und Ligand waren nötig, um die N‐Arylierungsprodukte unter milden Bedingungen zu bilden.…”