James, Michael John orcid.org/0000-0003-2591-0046, Clarke, George, Fairlamb, Ian James Stewart orcid.org/0000-0002-7555-2761 et al. (1 more author) (2022) Safe Handling of Air-Sensitive Organometallic Reagents Using Schlenk Line Techniques: Negishi Cross-Couplings for Trainee Graduate Students. JOURNAL OF CHEMICAL EDUCATION. pp. 2656-2660. ISSN 0021-9584
Abstract
A laboratory experiment has been devised to train new graduate trainees in the safe and controlled handling of air-sensitive organometallic reagents using Schlenk lines, high vacuum pumps, liquid nitrogen traps, and cannula transfers. The reaction involves the formation of air-, moisture-, and thermally sensitive 2-pyridyllithium, generated in situ by the reaction of 2-bromopyridine with n-butyllithium in dry THF at −78 °C. Subsequent transmetalation with dried ZnCl2 and reaction with 4-bromo-6-methyl-2-pyrone in the presence of catalytic Pd(PPh3)4 afforded the heterobiaryl product, 4-(2′-pyridyl)-6-methyl-2-pyrone. The many sensitivities of this experiment serve to provide an excellent practical demonstration for new graduate trainees of what can go wrong when experimental procedures are not accurately followed.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2022 The Authors |
Keywords: | Problem Solving/Decision Making,Hands-On Learning/Manipulatives,Safety/Hazards,Graduate Education/Research Organic Chemistry |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 31 Aug 2022 15:00 |
Last Modified: | 22 Jan 2025 00:20 |
Published Version: | https://doi.org/10.1021/acs.jchemed.2c00134 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1021/acs.jchemed.2c00134 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:190493 |
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Description: Safe Handling of Air-Sensitive Organometallic Reagents Using Schlenk Line Techniques: Negishi Cross-Couplings for Trainee Graduate Students
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