Science of Synthesis

Sammakia, T.; Abramite, J. A.; Sammons, M. F., Science of Synthesis, (2007) 33, 416.

The most general cross-coupling method for the synthesis of enamines uses alk-1-enyl bromides as the coupling partner.[‌59‌,‌60‌] Both tris(dibenzylideneacetone)dipalladium and palladium(II) acetate in conjunction with rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl are effective catalytic systems, where the catalyst loadings range from 1–3 mol% palladium (and 2–6 mol% for the BINAP ligand). Performing the reactions at elevated temperatures (80–100°C) in toluene with sodium tert-butoxide as the base provides the best results. A variety of alk-1-enyl bromides and secondary amines are successfully coupled under these conditions to provide enamines ‌40‌ (‌Scheme 21‌).

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References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88-8, 8888.
• 8.Meeeee-Meee, (8888) M 88-8, 888.