Copper-Catalyzed N-Arylation of 2-Imidazolines with Aryl Iodides

Abstract

The first copper-catalyzed N-arylation of 2-imidazolines is described. The reaction affords compounds with desirable lead-like characteristics in high yield with practical simplicity under inexpensive, "ligand-free" conditions. The cross coupling was successful with electron-rich and electron-poor aromatic iodides. Substrates bearing halides, esters, nitriles, and free hydroxyls are well tolerated, providing reactive handles for further functionalization, as are pyridines. In addition, the regioselective N-arylation of a 4-substituted imidazoline is reported.

Cascade Chan‐Lam C−O Coupling/[3,3]‐Rearrangement of Arylhydroxylamines with Arylboronic Acids Toward NOBIN Analogues

“…In 1998, Chan, Lam and Evans reported a mild copper‐promoted carbon‐hetero cross‐coupling reaction between amines and arylboronic acids to generate the corresponding N ‐arylated products [4] . Over the past few decades, this coupling reaction has been studied with various nitrogen nucleophiles [5] , such as amides, sulfoximines, amidines, azides, hydrazines and different heterocyles, and a variety of organoboron reagents [5a–j,6] , such as arylboric acids, arylboric esters and arylborates. It is worth mentioning that oxygen nucleophiles could also be employed in this reaction for the synthesis of O ‐arylated products [4,7] …”

Chemoselective Deprotection of Sulfonamides Under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications

“…Following general procedure IV using 50 (140 mg, 0.36 mmol, 1.0 equiv) and TfOH (0.035 mL, 0.4 mmol, 1.1 equiv) at 90 °C for 24 h. Purification of the crude product by flash column chromatography (SiO 2 DCM:MeOH 10:1) afforded 51 (55 mg, 70%). 1 H and 13 C NMR data are identical to those reported in the literature …”

2-(Aryl-sulfonyl)oxetanes as designer 3-dimensional fragments for fragment screening: synthesis and strategies for functionalisation

“…14 We are interested in the preparation of novel non-planar fragments, with desirable properties, which contain biologically important motifs, and access new areas of chemical space. 15 Consequently we designed 2-sulfonyl oxetanes ( Fig. 1), as non-planar fragments to comply with the rule-of-3, modified for the number of hydrogen bond acceptors (HBA).…”