Palladium-Catalyzed Remote Hydrosulfonamidation of Alkenes: Access to Primary N-Alkyl Sulfamides by the SuFEx Reaction,Journal of the American Chemical Society

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Palladium-Catalyzed Remote Hydrosulfonamidation of Alkenes: Access to Primary N-Alkyl Sulfamides by the SuFEx Reaction
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2024-05-02 , DOI: 10.1021/jacs.4c03283
Chuanqi Hou ₁ , Zhenye Liu ₂ , Lan Gan ₁ , Wenzheng Fan ₁ , Lin Huang ₁ , Pinhong Chen ₁ , Zheng Huang ₁ , Guosheng Liu _{1,

2}

Affiliation

Herein, we establish a remote hydrosulfonamidation (HSA) of alkenes using palladium catalysis, where N-fluoro-N-(fluoro-sulfonyl)-carbamate with a sulfur(VI) fluoride moiety is demonstrated as a good amidation reagent. The anti-Markovnikov HSA reaction of terminal alkenes and the remote HSA of internal alkenes are achieved to efficiently yield primary N-alkyl-N-(fluorosulfonyl)-carbamates. In addition, this protocol enables the high-value utilization of alkane by combining the dehydrogenation process. The generated N-alkyl products exhibit a unique reactivity of sulfur(VI) fluorides, which can be directly transferred to N-alkyl sulfamides or amines via the sulfur(VI) fluoride exchange reaction, thereby streamlining their synthesis. Moreover, a (pyridyl) benzazole-type ligand proved to be vital for the excellent chemo- and regioselectivities.

中文翻译：

钯催化烯烃远程氢磺酰胺化：通过 SuFEx 反应获得伯 N-烷基磺酰胺

在此，我们利用钯催化建立了烯烃的远程氢磺酰胺化（HSA），其中具有硫（VI）氟化物部分的N-氟-N- （氟磺酰基）-氨基甲酸酯被证明是一种良好的酰胺化试剂。实现末端烯烃的反马尔可夫尼科夫HSA反应和内部烯烃的远程HSA反应，有效地生成伯N-烷基-N- (氟磺酰基)-氨基甲酸酯。此外，该方案通过结合脱氢过程实现烷烃的高值利用。生成的N-烷基产物表现出独特的氟化硫(VI)反应活性，可以通过氟化硫(VI)交换反应直接转化为N-烷基磺酰胺或胺，从而简化其合成。此外，（吡啶基）苯并唑型配体被证明对于优异的化学和区域选择性至关重要。

更新日期：2024-05-02

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