A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides. Issue 43 (22nd October 2020)

• Record Type: Journal Article
• Authors: Sun, Wanwan; Chen, Xiaobei; Hu, Ying; Geng, Huihui; Jiang, Yuanrui; Zhou, Yuxin; Zhu, Wenjing; Hu, Min; Hu, Haohua; Wang, Xingyi; Wang, Xinli; Zhang, Shilei; Hu, Yanwei
• Is Part Of: Tetrahedron letters. Volume 61:Issue 43(2020)
• Publication Date: 2020-10-22
• Subjects: Sodium hydride -- Detosylation -- P-toluenesulfonamides -- Indole; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152442
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Mild reaction conditions and convenient operations. A broad substrate scope for various nitrogen-containing compounds and sulfonyl groups. Tosylation and detosylation could take place under same reaction conditions. Abstract: A NaH-mediated detosylation reaction of various Ts-protected indoles, azaheterocycles, anilines and dibenzylamine was reported. The method features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.