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Transition-metal-free hydroamination/defluorination/cyclization of perfluoroalkyl alkynes with amidines
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2021-11-16 , DOI: 10.1039/d1qo01439k
Li-Wen Sun 1 , Zi-Lun Yu 1 , Xin-Long Luo 1 , Mengtao Ma 2 , Zhi-Liang Shen 1 , Xue-Qiang Chu 1
Affiliation  

An efficient defluorinative net-[3 + 3]-cyclization strategy for the construction of perfluoroalkyl-substituted pyrimidine derivatives by using a series of perfluoroalkyl alkynes and amidines as starting materials was developed. The present reaction proceeded successfully under transition-metal-free conditions to form two new C–N bonds and a new heterocyclic ring through a sequence of hydroamination, defluorination, and annulation. The desired pyrimidines could be obtained with good functional group tolerance and moderate to good yields. Moreover, the distinctive fluorine effects of perfluoroalkyl substituents are vital for tuning the reactivity of alkynes for the anticipated defluorinative annulation. The pendant π system would lower associated bond dissociation energy significantly compared to that of a nonactivated C(sp3)–F bond.

中文翻译:

全氟烷基炔烃与脒的无过渡金属加氢胺化/脱氟/环化

开发了一种有效的脱氟净-[3 + 3]-环化策略,用于通过使用一系列全氟烷基炔烃和脒作为起始材料构建全氟烷基取代的嘧啶衍生物。本反应在不含过渡金属的条件下成功进行,通过加氢胺化、脱氟和成环的顺序形成了两个新的 C-N 键和一个新的杂环。可以获得具有良好官能团耐受性和中等至良好产率的所需嘧啶。此外,全氟烷基取代基的独特氟效应对于调节炔烃的反应性对于预期的脱氟环化至关重要。与未活化的 C(sp3 )–F 键。
更新日期:2021-12-01
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