Low Catalyst Loadings for Ligand‐Free Copper(I)‐Oxide‐Catalyzed N‐Arylation of Methanesulfonamide in Water

Abstract

A simple and practical protocol for the cross-coupling of methanesulfonamide and aryl iodides under ligand-free copper(I)-oxide-catalyzed conditions in water is reported. The[a] Natural

Iron-CatalyzedN-Arylsulfonamide Formation through Directly Using Nitroarenes as Nitrogen Sources

“…To obviate this drawback, the construction of N -arylsulfonamides via metal-catalyzed C–N bond formation has been extensively studied in the past few years (Scheme , path b). Such an approach includes the reactions of sulfonamides as nitrogen-based nucleophiles with aryl halides, alcohols, activated esters or arylboronic acids, and the aminosulfonation of hydrocarbons . This alternative route offers a straightforward strategy for the preparation of N -arylsulfonamides without the use of anilines; however, it is limited by the harsh conditions, requirement of additional bases and/or ligands, and comparatively complicated starting materials which must be first synthesized.…”

Palladium-Catalyzed Regiocontrolled Domino Synthesis of N-Sulfonyl Dihydrophenanthridines and Dihydrodibenzo[c,e]azepines: Control over the Formation of Biaryl Sultams in the Intramolecular Direct Arylation

“…The sulfonalides 20 – 32 were prepared by reacting anilines and sulfonyl chlorides . Under the optimized condition, the sulfonanilides 20 , 21 , and 22 containing an electron-donating or withdrawing group at the 2-position exhibit similar reactivity with 6 affording dihydrophenanthridines 33 – 35 in excellent yields (Table ). While the sulfonanilide 23 containing a substituent at the 4-position sustained similar reactivity with 6 yielding dihydrophenanthridine 36 in 92% yield, compound 24 afforded dihydrophenanthridine 37 in somewhat reduced yield.…”

A tunable pair electrochemical strategy for the synthesis of new benzenesulfonamide derivatives

“…Firstly, they use aromatic amines which are carcinogens 11 and secondly, they lead to impure products. Other important methods for the synthesis of N -arylsulfonamide derivatives is the reaction of sulfonamides as nucleophiles with some organic compounds such as halides 12–15 , alcohols 16–21 , aryl esters 22–24 and arylboronicacids 25–28 . In these methods although the problem of using aniline has been solved, but some disadvantages such as harsh reaction conditions, tedious workup, using metal catalysts, bases and/or ligands accompany these methods.…”