Highly Electron-Deficient Pyridinium-Nitrones for Rapid and Tunable Inverse-Electron-Demand Strain-Promoted Alkyne-Nitrone Cycloaddition,Organic Letters

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Highly Electron-Deficient Pyridinium-Nitrones for Rapid and Tunable Inverse-Electron-Demand Strain-Promoted Alkyne-Nitrone Cycloaddition
Organic Letters ( IF 4.9 ) Pub Date : 2019-06-28 00:00:00 , DOI: 10.1021/acs.orglett.9b01863
Praveen N. Gunawardene ₁ , Wilson Luo ₁ , Alexander M. Polgar ₁ , John F. Corrigan ₁ , Mark S. Workentin ₁

Affiliation

Highly accelerated inverse-electron-demand strain-promoted alkyne-nitrone cycloaddition (IED SPANC) between a stable cyclooctyne (bicyclo[6.1.0]nonyne (BCN)) and nitrones delocalized into a C_α-pyridinium functionality is reported, with the most electron-deficient “pyridinium-nitrone” displaying among the most rapid cycloadditions to BCN that is currently reported. Density functional theory (DFT) and X-ray crystallography are explored to rationalize the effects of N- and C_α-substituent modifications at the nitrone on IED SPANC reaction kinetics and the overall rapid reactivity of pyridinium-delocalized nitrones.

中文翻译：

高度缺电子的吡啶-亚硝基，用于快速和可逆的电子需求逆向应变促进的炔烃-硝酮环加成反应

稳定环辛间离域到高加速逆电子需求张力促进炔环加成硝酮（IED SPANC）（双环[6.1.0]壬炔（BCN））和硝酮Ç _α -吡啶鎓官能度被报告，以最电子缺乏的“吡啶-硝基”在目前报道的BCN最快速的环加成反应中显示。密度泛函理论（DFT）和X-射线晶体学进行了探索合理化的效果Ñ -和C ^ _α在上IED SPANC反应动力学和吡啶鎓离域硝酮的整体快速反应性的硝酮-取代的修改。

更新日期：2019-06-28

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