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33.4.6.1.3.1 Variation 1: Of Bromides

DOI: 10.1055/sos-SD-033-00516

Sammakia, T.; Abramite, J. A.; Sammons, M. F.Science of Synthesis, (200733416.

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 13mol% palladium (and 26mol% for the BINAP ligand). Performing the reactions at elevated temperatures (80100°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


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