Front Cover: Synthesis of Sulfenamides from Benzoazole-2-thiones with Primary and Secondary Amines using Triphenylbismuth Dichloride-Mediated S−N Bond Formation Reaction (Asian J. Org. Chem. 8/2024)

Abstract

The cover design showcases a general method for the synthesis of sulfenamides from various benzoazole-2-thiones with amines using bismuth reagent. The brother′s azole-thiones and the sister′s amines being reacted with the bismuth reagent to produce the sulfenamide that blooms beautifully like fireworks. In the night sky, the S-N bond formation is depicted to resemble the Milky Way. The reactions of benzoazole-2-thiones with various primary or secondary amines in the presence of triphenylbismuth dichloride (Ph3BiCl2) at 60 °C in DMSO under aerobic conditions afforded the corresponding sulfenamides in moderate-to-excellent yields. This reaction is the first example of an efficient S–N bond formation reaction utilizing a lowtoxicity pentavalent organobismuth reagent under mild reaction conditions. The reaction will likely be applied to develop compounds with medicinal value or industrial utility. More information can be found in article number e202400138 by Yuki Murata, Shuji Yasuike, and co-workers.