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Updated: Sep 21, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Computational insights into strain-increase allylborations for alkylidenecyclopropanes
Lingfei Hu1, Han Gao1, Yanlei Hu1
1School of Chemistry and Chemical Engineering, Key Laboratory of Colloid and Interface Chemistry, Ministry of Education, Shandong University, Jinan, Shandong, 250100, China. ganglu@sdu.edu.cn.
Computational studies revealed that increasing boron center acidity enhances strain-increase allylborations. This improvement overcomes weak electronic interactions and steric hindrance, boosting reactivity in organic synthesis.
Area of Science:
- Organic Chemistry
- Computational Chemistry
Background:
- Allylborations are key reactions in organic synthesis.
- Vinylcyclopropyl boronates exhibit low reactivity due to electronic and steric factors.
Purpose of the Study:
- Investigate the origins of reactivity in strain-increase allylborations.
- Determine methods to enhance the efficiency of these reactions.
Main Methods:
- Computational investigation using density functional theory (DFT).
- Analysis of electronic interactions and steric effects.
Main Results:
- Low reactivity of vinylcyclopropyl boronates stems from weak electronic interactions.
- Increased boron center acidity significantly improves reactivity.
- Stronger O→B interactions compensate for destabilizing steric effects.
Conclusions:
- Acidity modulation is a viable strategy to enhance allylboration reactivity.
- Understanding electronic and steric effects guides the design of more efficient boron reagents.
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