Metal ions and complexes in organic reactions. Part XVI. Extension of copper-catalysed Gabriel reactions to vinylic halides and to analogues of phthalimide salts

Abstract

Catalysed conversions of vinylic bromides, RCH:CHBr (R = H, alkyl, or aryl) into the corresponding phthalimidocompounds were effected in a reaction system [KN(CO)₂C₆H₄+ Cul + MeCO·NMe₂ at 165°] previously found suitable for aryl halides; some mechanistic features are indicated. The response of aromatic-type heterocyclic bromides is also exemplified. Analogously, the sodium salts of succinimide, maleimide, dibenzamide, benzenesulphonamide, and benzenesulphonanilide formed N-phenyl derivatives, but were less reactive than sodium phthalimide.