ArticleAdvanced science (Weinheim, Baden-Wurttemberg, Germany)2023
Regioselective Electrophilic Addition to Propargylic B(MIDA)s Enabled by β-Boron Effect.
Article in Advanced science (Weinheim, Baden-Wurttemberg, Germany), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
3 citing papers in PubMed.
- (Poly)Borylated Species as Modern Reactive Groups toward Unusual Synthetic Applications.Angewandte Chemie (International ed. in English) · 2026Review
- Harnessing the β-boron effect for regioselective Ru-catalyzed hydrosilylation of internal alkynes.Nature communications · 2025Article
- Regioselective Electrophilic Addition to Propargylic B(MIDA)s Enabled by β-Boron Effect.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
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Authors and funding
8 authors.
Funding
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.
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