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Frustrated Lewis Pair-Mediated Cycloisomerization of Propargylaniline and Aryl Propargyl Ether Derivatives via a 6-endo-dig Cyclization/Dehydrogenation Sequence
Organic Letters ( IF 4.9 ) Pub Date : 2024-11-20 , DOI: 10.1021/acs.orglett.4c03817 Pei Liang, Yapeng Cai, Hong Zhang, Tongdao Wang
Organic Letters ( IF 4.9 ) Pub Date : 2024-11-20 , DOI: 10.1021/acs.orglett.4c03817 Pei Liang, Yapeng Cai, Hong Zhang, Tongdao Wang
An efficient FLP-mediated cycloisomerization is described, providing easy access to quinolinium and chromenylium derivatives by treatment of readily available propargylanilines and aryl propargyl ethers with Lewis acidic boranes, respectively. The reaction proceeds via a 6-endo-dig cyclization/dehydrogenation sequence. The heteroatom functions serve as Lewis bases in combination with Lewis acidic boranes to effect synergistic activation of an alkynyl triple bond and a C–H bond.
中文翻译:
通过 6-endo-dig 环化/脱氢序列实现炔丙基苯胺和芳基炔基醚衍生物的 Lewis 对介导的环异构化
描述了一种高效的 FLP 介导的环异构化,通过分别用 Lewis 酸性硼烷处理现成的炔丙基苯胺和芳基炔丙基醚,可以轻松获得喹啉和铬基衍生物。反应通过 6-endo-dig 环化/脱氢序列进行。杂原子功能作为 Lewis 碱与 Lewis 酸性硼烷结合,以实现炔基三键和 C-H 键的协同激活。
更新日期:2024-11-20
中文翻译:
通过 6-endo-dig 环化/脱氢序列实现炔丙基苯胺和芳基炔基醚衍生物的 Lewis 对介导的环异构化
描述了一种高效的 FLP 介导的环异构化,通过分别用 Lewis 酸性硼烷处理现成的炔丙基苯胺和芳基炔丙基醚,可以轻松获得喹啉和铬基衍生物。反应通过 6-endo-dig 环化/脱氢序列进行。杂原子功能作为 Lewis 碱与 Lewis 酸性硼烷结合,以实现炔基三键和 C-H 键的协同激活。