Sulfur-Arylation of Sulfenamides via Ullmann-Type Coupling with (Hetero)aryl Iodides.
Sulfur-Arylation of Sulfenamides via Ullmann-Type Coupling with (Hetero)aryl Iodides.
复制标题
通过与（杂）芳基碘化物的乌尔曼型偶联进行亚磺酰胺的硫芳基化。
DOI：
10.1021/acs.orglett.3c01874
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发表时间：
2023
期刊：
影响因子：
5.2
通讯作者：
Ellman,JonathanA
中科院分区：
文献类型：
--
作者：
Greenwood,NathanielS;Ellman,JonathanA
报道了以廉价的碘化铜为催化剂，通过Ullmann型偶联反应使亚硫酰胺与工业上丰富的(杂)芳基碘化物发生硫杂芳基化反应。反应输入的范围很广，包括芳基和烷基亚硫酰胺，以及空间位阻很高的芳基和5-和6元环杂芳基碘。报道了与许多生物活性高氧化态硫化物相关的FS-甲基亚硫酰胺的(杂化)芳基化反应，包括复杂的芳基碘化合物。还公开了缺乏电子的S-杂芳基磺亚胺的微笑重排。
Sulfur-(hetero)arylation of sulfenamides with commercially abundant (hetero)aryl iodides by Ullmann-type coupling with inexpensive copper(I) iodide as the catalyst is reported. A broad scope of reaction inputs was demonstrated, including both aryl and alkyl sulfenamides and highly sterically hindered aryl and 5- and 6-membered ring heteroaryl iodides. Relevant to many bioactive high oxidation state sulfur compounds, the (hetero)arylation ofS-methyl sulfenamides is reported, including for complex aryl iodides. Smiles rearrangement of electron-deficientS-heteroaryl sulfilimines is also disclosed.