65523-64-0Relevant academic research and scientific papers
Ruthenium-Catalyzed Remote C-H Sulfonylation of N-Aryl-2-aminopyridines with Aromatic Sulfonyl Chlorides
Ramesh, Balu,Jeganmohan, Masilamani
, p. 6000 - 6003 (2017)
A ruthenium-catalyzed remote sulfonylation at the C5 position of the pyridine group of N-aryl-2-aminopyridines with aromatic sulfonyl chlorides is described. The mechanistic and deuterium labeling studies clearly reveal that the ruthenametallacycle is a key intermediate in the reaction, which forms via the C-H bond activation. The DFT calculation supports that the C5 position of the 2-aminopyridine group carries a more negative charge (-0.304) as compared with other carbons in the metalacycle intermediate.
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.
