(1E,3E,5Z)-1,6-Dibromohexa-1,3,5-triene: regio- and stereocontrolled mono pallado-catalysed cross-coupling reactions

Pierre Villiers (1) , Nicolas Vicart (1) , Yvan Ramondenc (2) , Gérard Plé (2)

1 IRCOF - Institut de Chimie Organique Fine
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

We describe the regio- and stereocontrolled synthesis of (Z,E,E)-α-bromo-ω-substituted hexatrienes. The synthesis is based on a mono pallado-catalysed cross-coupling reaction between (1E,3E,5Z) isomer of 1,6-dibromohexa-1,3,5-triene and various organozinc reagents. Mono pallado-catalysed cross-coupling reaction from (1E,3E,5Z)-1,6-dibromohexa-1,3,5-triene and various organozinc reagents has given regio- and stereoselectively conjugated (Z,E,E)-α-bromo-ω-substituted hexatrienes.

Keywords: palladium palladium; coupling reactions; trienes; zinc compounds; compounds; zinc

Domains: Chemical Sciences; Chemical Sciences; Catalysis; Chemical Sciences; Material chemistry; Chemical Sciences; Organic chemistry

Pierre Villiers, Nicolas Vicart, Yvan Ramondenc, Gérard Plé. (1E,3E,5Z)-1,6-Dibromohexa-1,3,5-triene: regio- and stereocontrolled mono pallado-catalysed cross-coupling reactions. Tetrahedron Letters, 1999, 40 (50), pp.8781-8784. ⟨10.1016/S0040-4039(99)01670-6⟩. ⟨hal-02385850⟩