✓Execute Mizoroki-Heck cross-coupling reactions under mild conditions
✓Characterize coupling products and optimize reaction yields
Protocol
Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium [(P(NC5H10)3)2Pd(Cl)2] (1) is an easy accessible, cheap, and air stable, but highly active Heck catalyst with an excellent functional group tolerance that efficiently operates under mild reaction conditions to give the coupling products in very high yields.
Difficulty
advanced
Total time
~8–12 hours (ligand synthesis ~4 hrs, catalyst synthesis ~2 hrs, Heck reactions ~2–4 hrs depending on scale and workup)
Prepare the bulky phosphine ligand via condensation or coordination chemistry from phosphorus precursor and piperidine derivatives. This ligand imparts steric and electronic properties critical for catalyst activity.
Complex the phosphine ligand with palladium dichloride precursor to generate the air-stable, highly active Heck catalyst. Isolate and characterize the product.
▶ 04:18
3
Execute Mizoroki-Heck cross-coupling under mild conditions
Perform C–C coupling between organic halide and alkene substrates in the presence of base and the palladium catalyst at low temperature. Monitor reaction progress by TLC or HPLC.
▶ 06:02
4
Isolate and characterize Heck coupling products
Workup reaction mixture, purify coupling products via column chromatography or precipitation, and confirm structure and purity by NMR, MS, or HPLC analysis.
▶ 09:17
💬 Comments coming soon
New protocols and pitfalls, in your inbox
A short email when we add notable lab videos and failure cases. No spam, unsubscribe anytime.