Transition‐Metal‐Free Olefinic C−H Azidoalkylthiolation via C(sp3)−S Bond Cleavage of Vinylsulfonium Salts. Issue 17 (9th August 2022)

• Record Type: Journal Article
• Authors: He, Yuan; Huang, Zilong; Ma, Juan; Lin, Jie; Zhou, Yong‐Gui; Yu, Zhengkun
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 17(2022)
• Page Start: 3023
• Page End: 3034
• Publication Date: 2022-08-09
• Subjects: azidoalkylation -- vinyl sulfonium salts -- C(sp3)−H functionalization -- sodium azide -- C(sp3)−S cleavage; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200529
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A transition‐metal‐free olefinic C−H azidoalkylthiolation protocol was developed through C( sp 3 )−S bond cleavage of vinylsulfonium salts with sodium azide in air under aqueous conditions. An interrupted Pummerer/nucleophilc azidoalkylation cascade was developed for such a process. The practicability of the synthetic protocol was demonstrated by scale‐up preparation of the azidoalkylthiolated tetrasubstituted alkene products and their transformations to diverse triazole and tetrazole derivatives as well as azidoalkylthio‐funtionalized N ‐heterocyclic compounds. The present synthetic methodology features broad substrate scopes and good functional group tolerance under mild conditions. Abstract :