ArticleAngewandte Chemie (International ed. in English)2023
Trimethylsilyl Chloride Aids in Solubilization of Oxidative Addition Intermediates from Zinc Metal.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
What it found
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
6 citing papers in PubMed, 12 citations in OpenAlex.
- Palladium Black from Decomposition Is a Directly Reusable Catalyst.ACS catalysis · 2026Article
- Lack of Evidence Supporting Widespread Use of 1,2-Dibromoethane as an Activator for Zinc: Alternative Stirring or TMSCl Activation.Journal of the American Chemical Society · 2026Article
- A DMAP-enabled strategy for C(spNature communications · 2025Article
- Three-Phase Emulsions during Cross-Coupling Reactions in Water.The Journal of organic chemistry · 2025Article
- Mechanisms of Activating Agents to Form Organozinc Reagents from Zinc Metal: Lessons for Reaction Design.The Journal of organic chemistry · 2025Review
- Metal Activation Produces Different Reaction Environments for Intermediates during Oxidative Addition.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Trimethylsilyl chloride (TMSCl) is commonly used to "activate" metal(0) powders toward oxidative addition of organohalides, but knowledge of its mechanism remains limited by the inability to characterize chemical intermediates under reaction conditions. Here, fluorescence lifetime imaging microscopy (FLIM) overcomes these prior limitations and shows that TMSCl aids in solubilization of the organozinc intermediate from zinc(0) metal after oxidative addition, a previously unknown mechanistic role. This mechanistic role is in contrast to previously known roles for TMSCl before the oxidative addition step. To achieve this understanding, FLIM, a tool traditionally used in biology, is developed to characterize intermediates during a chemical reaction-thus revealing mechanistic steps that are unobservable without fluorescence lifetime data. These findings impact organometallic reagent synthesis and catalysis by providing a previously uncharacterized mechanistic role for a widely used activating agent, an understanding of which is suitable for revising activation models and for developing strategies to activate currently unreactive metals.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.