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由硫化物一锅法合成α-碘代磺胺肟

One-Pot Synthesis of -Iodo Sulfoximines from Sulfides.

作者信息

Zupanc Anže, Jereb Marjan

机构信息

Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia.

出版信息

J Org Chem. 2021 Apr 16;86(8):5991-6000. doi: 10.1021/acs.joc.1c00292. Epub 2021 Mar 25.

Abstract

This is the first report on the synthesis and characterization of -iodo sulfoximines. The synthesis was designed as a room temperature one-pot cascade reaction from readily available sulfides as starting compounds, converted into sulfoximines by reaction with ammonium carbonate and (diacetoxyiodo)benzene, followed by iodination with -iodosuccinimide or iodine , in up to 90% isolated yields, also at a multigram scale. Iodination of aryls with -iodo sulfoximines, oxidation, and conversion to -SCF congeners have been demonstrated.

摘要

这是关于碘代磺胺氧化亚胺的合成与表征的首份报告。该合成设计为在室温下从易于获得的硫化物作为起始化合物进行一锅法串联反应,通过与碳酸铵和(二乙酰氧基碘)苯反应转化为磺胺氧化亚胺,随后用碘代琥珀酰亚胺或碘进行碘化,分离产率高达90%,甚至在多克规模下也能实现。已证明用碘代磺胺氧化亚胺对芳基进行碘化、氧化以及转化为-SCF同系物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8c0a/8154609/4bfe8dfd0834/jo1c00292_0001.jpg

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