Details

Autor(en) / Beteiligte

• James, Michael J.
• Clarke, George E.
• Lee, Charlotte
• Fairlamb, Ian J. S.

Titel

Safe Handling of Air-Sensitive Organometallic Reagents Using Schlenk Line Techniques: Negishi Cross-Couplings for Trainee Graduate Students

Ist Teil von

• Journal of chemical education, 2022-07, Vol.99 (7), p.2656-2660

Ort / Verlag

Easton: American Chemical Society and Division of Chemical Education, Inc

Erscheinungsjahr

2022

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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.