ArticleNature chemistry2016
MIDA boronates are hydrolysed fast and slow by two different mechanisms.
Article in Nature chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed.
- Kinetically Stable Boron-Heteroatom Bonds.Angewandte Chemie (International ed. in English) · 2026Article
- Pure Gaussian Apodisation Reduces Integral Crosstalk Sensitivity in Quantitative NMR.Magnetic resonance in chemistry : MRC · 2026Article
- Goldilocks boronic esters: optimized properties through understanding hydrolysis kinetics.Chemical science · 2026Article
- Ligand-Enabled Selective Coupling of MIDA Boronates to Dehydroalanine-Containing Peptides and Proteins.Journal of the American Chemical Society · 2025Article
- Simple Parameters and Data Processing for Better Signal-to-Noise and Temporal Resolution inThe Journal of organic chemistry · 2024Article
- Weak Base-Promoted Direct Cross-Coupling of Naphthalene-1,8-diaminato-substituted Arylboron Compounds.JACS Au · 2024Article
- Derivatization of 2,1,3-Benzothiadiazole via Regioselective C-H Functionalization and Aryne Reactivity.The Journal of organic chemistry · 2024Article
- Reactivity of 1,3-enyne MIDA boronates: exploration of novel 1,2-alkyne shiftChemical science · 2024Article
- Modular Synthesis of Complex Benzoxaboraheterocycles through Chelation-Assisted Rh-Catalyzed [2 + 2 + 2] Cycloaddition.ACS catalysis · 2024Article
- PdNPs/NiNWs as a welding tool for the synthesis of polyfluorene derivatives by Suzuki polycondensation under microwave radiation.Scientific reports · 2024Article
- Emerging Trends in Cross-Coupling: Twelve-Electron-Based LChemical reviews · 2022Review
- Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group.Angewandte Chemie (International ed. in English) · 2022Article
- A Modular Synthesis of Teraryl-Based α-Helix Mimetics, Part 5: A Complete Set of Pyridine Boronic Acid Pinacol Esters Featuring Side Chains of Proteinogenic Amino Acids.European journal of organic chemistry · 2022Article
- Article
- Synthesis of 2-BMIDA Indoles via Heteroannulation: Applications in Drug Scaffold and Natural Product Synthesis.Organic letters · 2022Article
- Preparation of MIDA Anhydride and Reaction with Boronic Acids.Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2022Article
- Electrophilic Fluorination of Alkenes via Bora-Wagner-Meerwein Rearrangement. Access to β-Difluoroalkyl Boronates.Angewandte Chemie (International ed. in English) · 2021Article
- The 2-Pyridyl Problem: Challenging Nucleophiles in Cross-Coupling Arylations.Angewandte Chemie (International ed. in English) · 2021Review
- Article
- Reductive α-borylation of α,β-unsaturated esters using NHC-BHChemical science · 2019Article
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Abstract
MIDA boronates (N-methylimidodiacetic boronic acid esters) serve as an increasingly general platform for small-molecule construction based on building blocks, largely because of the dramatic and general rate differences with which they are hydrolysed under various basic conditions. Yet the mechanistic underpinnings of these rate differences have remained unclear, which has hindered efforts to address the current limitations of this chemistry. Here we show that there are two distinct mechanisms for this hydrolysis: one is base mediated and the other neutral. The former can proceed more than three orders of magnitude faster than the latter, and involves a rate-limiting attack by a hydroxide at a MIDA carbonyl carbon. The alternative 'neutral' hydrolysis does not require an exogenous acid or base and involves rate-limiting B-N bond cleavage by a small water cluster, (H
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