Efficient Manganese/Copper Bimetallic Catalyst for N‐Arylation of Amides and Sulfonamides Under Mild Conditions in Water

Abstract

An efficient and mild method using a bimetallic MnF2/CuI catalyst at 60 °C in water was developed for the N‐arylation of amides and sulfonamides with aryl halides. A variety of functionalized amides and sulfonamides were coupled with different substituted aryl halides to afford the corresponding N‐arylated products in good to excellent yields (up to 97 %).

Potassium Carbonate Promoted C–N Coupling Reaction between Benzamides and Aryl Iodides

“…Unfortunately, when 1-iodo-4-methoxybenzene, aryl bromide, and other functionalized iodobenzene were employed as substrates, no corresponding products were obtained (Table 2, entries 13, 21, 22-24). To highlight the utilization of this reaction, the use of heterocyclic compounds as substrates for this reaction was also investigated, which to our delight, furnished the corresponding N-arylated amides in moderate yields as well (entries [14][15][16][17][18][19].…”

Recent Functionalizations of Primary Sulfonamides

“…N-Arylsulfonamides are important synthetic building blocks that are prevalent in many bioactive compounds and medicinal agents, and these compounds have important roles in organic synthesis and biological and pharmaceutical research. 199 The vast majority of N-arylated sulfonamides are prepared via the reaction of sulfonyl chlorides with excess primary or secondary amines. However, drawbacks of this methodology are the limited availability of sulfonyl chlorides and that many aromatic amines carry a genotoxic hazard.…”

“…[203][204][205][206][207] In 2013, Teo and coworkers reported an efficient bimetallic manganese/copper catalyst for the N-arylation of amides and sulfonamides under mild conditions in water (not shown). 199 Also employing water as solvent, Kaboudin and coworkers used an iron(II,III) oxide magnetic-nanoparticle-…”

Manganese‐Catalyzed Cross‐Coupling Processes

“…In order to lower the reaction temperatures in the above presented reactions and to further broaden the substrate scope a bimetallic system MnF2/CuI was subsequently developed (Scheme 39) [40]. Under these conditions many C-N coupling reactions proceeded at 60 °C.…”

“…Scheme 39. Mn/Cu co-catalyzed N-arylation of benzamides and sulfonamides with various substituted aryl iodides in water [40].…”