钌催化的腈氧化物与富电子炔烃的[3 + 2]环加成反应，具有反向区域选择性。
Ru-Catalyzed [3 + 2] Cycloaddition of Nitrile Oxides and Electron-Rich Alkynes with Reversed Regioselectivity.
作者信息
Feng Qiang, Huang Hai, Sun Jianwei
机构信息
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
出版信息
Org Lett. 2021 Apr 2;23(7):2431-2436. doi: 10.1021/acs.orglett.1c00273. Epub 2021 Mar 22.
Polarity reversal ("umpolung") of a functional group can override its inherent reactivity and lead to distinct bond-forming modes. Herein we describe a rarely studied cycloaddition between nitrile oxides and electron-rich alkynes with reversed regioselectivity, leading to the useful 4-heterosubstituted isoxazoles. The use of a ruthenium catalyst completely overrides the inherent polarity of nitrile oxides. This reversed regioselectivity was also observed for their reactions with a range of electron-deficient alkynes.
官能团的极性反转（“极性翻转”）可以改变其固有的反应活性，并导致不同的成键模式。在此，我们描述了一种鲜少被研究的腈氧化物与富电子炔烃之间的环加成反应，该反应具有相反的区域选择性，可生成有用的4-杂取代异恶唑。钌催化剂的使用完全改变了腈氧化物固有的极性。在它们与一系列缺电子炔烃的反应中也观察到了这种相反的区域选择性。
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