A new reactivity pattern for vinyl bromides: cine-substitution via palladium catalysed C-N coupling/Michael addition reactions.
Palladium catalysed C-N bond formation can be used to convert vinyl bromides to the corresponding enamines, which are reacted in situ with alkylidene malonates to provide Michael adducts. The overall transformation results in cine-substitution of the starting vinyl bromide.
Willis
Michael C
MC
Department of Chemistry, University of Bath, Bath BA2 7AY, UK. m.c.willis@bath.ac.uk
Chauhan
Jay
J
Whittingham
William G
WG
D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D004952:Esters; D007659:Ketones; D014753:Vinyl Compounds; D010165:Palladium; C003763:vinyl bromide