Regioselective Electrophilic Addition to Propargylic B (MIDA) s Enabled by β ‐Boron Effect
Abstract: Electrophilic addition reaction to alkynes is of fundamental importance in organic chemistry, yet the regiocontrol when reacting with unsymmetrical 1,2‐dialkyl substituted alkynes is often problematic. Herein, it is demonstrated that the rarely recognized β‐boron effect can confer a high level of site‐selectivity in several alkyne electrophilic addition reactions. A broad range of highly functionalized and complex organoborons are thus formed under simple reaction conditions starting from propargylic MIDA (N‐methyliminodiacetic acid) boronates. These products are demonstrated to be valuable building blocks in organic synthesis. In addition to the regiocontrol, this study also observes a drastic rate enhancement upon B (MIDA) substitution. Theoretical calculation reveals that the highest occupied molecular obital (HOMO) energy level of propargylic B (MIDA) is significantly raised by 0.3 eV, and the preferential electrophilic addition to the γ position is due to its higher HOMO orbital coefficient and more negative natural bond orbital (NBO) charge compared to the β position. This study demonstrates the potential of utilizing the β‐boron effect in stereoelectronic control of chemical transformations, which can inspire further research in this area.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Regioselective Electrophilic Addition to Propargylic B (MIDA) s Enabled by β ‐Boron Effect ; day:26 ; month:08 ; year:2023 ; extent:9
Advanced science ; (26.08.2023) (gesamt 9)
- Creator
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Li, Yin
Chen, Zhi‐Hao
Lin, Shuang
Liu, Yuan
Qian, Jiasheng
Li, Qingjiang
Huang, Zhi‐Shu
Wang, Honggen
- DOI
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10.1002/advs.202304282
- URN
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urn:nbn:de:101:1-2023082715030448512277
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:45 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Li, Yin
- Chen, Zhi‐Hao
- Lin, Shuang
- Liu, Yuan
- Qian, Jiasheng
- Li, Qingjiang
- Huang, Zhi‐Shu
- Wang, Honggen
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