Highly Electron-Deficient Pyridinium-Nitrones for Rapid and Tunable inverse-Electron-Demand Strain-Promoted Alkyne-Nitrone Cycloaddition

被引：12
作者：
Gunawardene, Praveen N. [1 ,2 ]
Luo, Wilson [1 ,2 ]
Polgar, Alexander M. [1 ,2 ]
Corrigan, John F. [1 ,2 ]
Workentin, Mark S. [1 ,2 ]
机构：
[1] Univ Western Ontario, Dept Chem, Richmond St, London, ON N6A 5B7, Canada
[2] Univ Western Ontario, Ctr Mat & Biomat Res, Richmond St, London, ON N6A 5B7, Canada
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 14期
基金：
加拿大自然科学与工程研究理事会;
关键词：
D O I：
10.1021/acs.orglett.9b01863
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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-a-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-a-substituent modifications at the nitrone on IED SPANC reaction kinetics and the overall rapid reactivity of pyridinium-delocalized nitrones.
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收藏
页码：5547 / 5551
页数：5
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