3989-43-3Relevant academic research and scientific papers
Mechanistic Insight Enables Practical, Scalable, Room Temperature Chan-Lam N-Arylation of N-Aryl Sulfonamides
Vantourout, Julien C.,Li, Ling,Bendito-Moll, Enrique,Chabbra, Sonia,Arrington, Kenneth,Bode, Bela E.,Isidro-Llobet, Albert,Kowalski, John A.,Nilson, Mark G.,Wheelhouse, Katherine M. P.,Woodard, John L.,Xie, Shiping,Leitch, David C.,Watson, Allan J. B.
, p. 9560 - 9566 (2018/09/27)
Sulfonamides are profoundly important in pharmaceutical design. C-N cross-coupling of sulfonamides is an effective method for fragment coupling and structure-activity relationship (SAR) mining. However, cross-coupling of the important N-arylsulfonamide pharmacophore has been notably unsuccessful. Here, we present a solution to this problem via oxidative Cu-catalysis (Chan-Lam cross-coupling). Mechanistic insight has allowed the discovery and refinement of an effective cationic Cu catalyst to facilitate the practical and scalable Chan-Lam N-arylation of primary and secondary N-arylsulfonamides at room temperature. We also demonstrate utility in the large scale synthesis of a key intermediate to a clinical hepatitis C virus treatment.
Facile N-arylation of amines and sulfonamides and O-arylation of phenols and arenecarboxylic acids
Liu, Zhijian,Larock, Richard C.
, p. 3198 - 3209 (2007/10/03)
An efficient, transition-metal-free procedure for the N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl inflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates a variety of functional groups.
Facile N-Arylation of Amines and Sulfonamides
Liu, Zhijian,Larock, Richard C.
, p. 4673 - 4675 (2007/10/03)
(Matrix presented) A facile, transition-metal-free N-arylation procedure for amines and sulfonamides has been developed, which affords good to excellent yields of arylated products under very mild reaction conditions. A methoxy-substituted aryl triflate affords N-arylated products in high yields with excellent regioselectivity. This chemistry tolerates a variety of functional groups.
Multinuclear NMR Study of Variously Substituted Sulphonamides and Sulphinamides
Ruosteuso, P.,Haekkinen, A.-M.,Mattila, T.
, p. 189 - 193 (2007/10/02)
13C, 15N and 17O NMR chemical shifts, and also 1J(CH) and 1J(NH) values, have been determined for variously substituted sulphonamides and some sulphinamides, either neat or in acetone or dimethyl sulphoxide solution.The effect of benzene ring substitutens on the chemical shifts of nitrogen and oxygen nuclei is slight, but N-substitution changes the shielding of both nuclei.Generally, an N-methyl substituent shields an amide nitrogen and an N,Ndimethyl substituent gives further slight shielding.On the other hand, an N-phenyl substituent deshilds the nitrogen strongly, but the deshielding effect of an N,N-diphenyl substituent is markedly smaller.The sulphonyl oxygens are deshilded relative to the sulphinyl oxygens, and N-methyl and N,N-dimethyl substituents shild the oxygen nucleus.The effect of N-phenyl and N,N-diphenyl substituents on the shielding of the oxygen atoms of the sulphonyl group is slight.The direct 1J(CH) coupling constants are similar, but they are characteristic of different type of sulphur amides.The 1J(NH) values are of the same order of magnitude for sulphonamides and sulphinamides, but are clearly smaller for N-unsubstituted amides than for N-substituted compounds.KEY WORDS Sulphonamide Sulphinamide Multinuclear NMR
