Tetrahedron
Tetrahedron
5 years ago

Sulfur-mediated C(sp2)–H imidation and 1,2-imidofluorination of vinyl sulfides

Sulfur-mediated C(sp2)–H imidation and 1,2-imidofluorination of vinyl sulfides
A new strategy for the C(sp2)–H imidation and 1,2-imidofluorination of vinylsulfides has been established through simple treatment with N-fluorobis(benzenesulfonyl)imide, which acts as both oxidant and nitrogen source. For alkyl and electron-rich aryl vinylsulfides, alkyl/arylthioenamines are produced in up to 92% total yields. However, for steric and electron-deficient aryl vinylsulfides, 1,2-imidofluorination products are prepared in up to 73% yields. The chemoselectivity is controlled by the steric and electronic effects of aryl substituents. Thionium ions are proposed as key intermediates in the two reactions.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017304507

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