Sulfonimidoyl Azide: A Novel Precursor for the Direct and Rapid Access to N‐Aryl Sulfonimidamides via Cu–Catalyzed Chan‐Evans‐Lam Reaction with Boronic Acids under Mild And Efficient Condition

• Published in: ChemistrySelect (Weinheim) Vol. 4; no. 47; pp. 14004 - 14006
• Main Authors: Ravindra, S., Rohith, J., Jesin, C. P. Irfana, Kataria, Ramesh, Nandi, Ganesh Chandra
• Format: Journal Article
• Language: English
• Published: 19-12-2019
• Subjects: Chan-Evans-Lam reaction; N-Aryl Sulfonimidamide; Sulfonimidoyl Azide; Suzuki- Miyuara reaction
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.201904548

Herein, we have introduced sulfonimidoyl azide as a precursor in a Cu‐catalyzed Chan‐Evans‐Lam reaction with aryl boronic acid for the synthesis of N‐aryl sulfonimidamide. The CuCl catalyzed reactions of sulfonimidoyl azides and aryl boronic acids have been proceeded in the presence of triethylamine (Et3N) as base in methanol at room temperature under oxygen atmosphere and resulted moderate to good yields of corresponding products in very short time. The synthetic utilities of N‐aryl sulfonimidamides have been established by iodination reactions and Suzuki‐Miyaura coupling reactions.
We introduced sulfonimidoyl azide as a novel precursor in a Cu‐catalyzed Chan‐Evans‐Lam reaction with aryl boronic acid for the synthesis of structurally diverse N‐aryl sulfonimidamides under mild and efficient reaction condition. The products were obtained in moderate to good yields in very short time. The synthetic utilities of N‐aryl sulfonimidamides were established by a base promoted iodination reactions and Suzuki‐Miyaura coupling reactions.