ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Mapping the Electronic Structure and the Reactivity Trends for Stabilized α-Boryl Carbanions.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed.
- (Poly)Borylated Species as Modern Reactive Groups toward Unusual Synthetic Applications.Angewandte Chemie (International ed. in English) · 2026Review
- Diastereodivergent electrophilic trapping of α-boryl lithium derivatives.Beilstein journal of organic chemistry · 2026Article
- Stereoselective Synthesis of Alkenyl Fluorides and Alkynes by Defluoro Coupling of Trifluoromethyl Arenes.Angewandte Chemie (International ed. in English) · 2025Article
- Vicinal Stereocenter Construction via α-Boryl Carbanions from Borylated Cyclopropanes.Journal of the American Chemical Society · 2025Article
- Article
- Selective Synthesis of α,α-Difluoro- and α-Monofluoro Methylene Substituted Arenes by Defluoro C-C Bond Coupling.Organic letters · 2025Article
- Cu-Catalyzed Chemoselective Borylcupration of Borylated (ACS catalysis · 2025Article
- Delocalization quantitatively mapped for prototypic organic nitroanions as well as azidoform anions.RSC advances · 2023Article
- Site-Selective (Z)-α-Borylalkenyl Copper Systems for Nucleophilic Stereodefined Allylic Coupling.Angewandte Chemie (International ed. in English) · 2022Article
- Mapping the Electronic Structure and the Reactivity Trends for Stabilized α-Boryl Carbanions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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Abstract
The chemistry of stabilized α-boryl carbanions shows remarkable diversity, and can enable many different synthetic routes towards efficient C-C bond formation. The electron-deficient, trivalent boron center stabilizes the carbanion facilitating its generation and tuning its reactivity. Here, the electronic structure and the reactivity trends of a large dataset of α-boryl carbanions are described. DFT-derived parameters were used to capture their electronic and steric properties, computational reactivity towards model substrates, and crystallographic analysis within the Cambridge Structural Dataset. This study maps the reactivity space by systematically varying the nature of the boryl moiety, the substituents of the carbanionic center, the number of α-boryl motifs, and the metal counterion. In general, the free carbanionic intermediates are described as borata-alkene species with C-B π interactions polarized towards the carbon. Furthermore, it was possible to classify the α-boryl alkylidene metal precursors into three classes directly related to their reactivity: 1) nucleophilic borata-alkene salts with alkali and alkaline earth metals, 2) nucleophilic η
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