Copper-catalyzed cross-coupling of (Z)-allyl phenyl ethers with Grignard compounds in the synthesis of insect pheromones

(8 Z )-Dodec-8-en-1-yl acetate (pheromone of oriental fruit moth Grapholita molesta ) and (9 Z )-dodec-9-en-1-yl acetate (pheromone of grape berry moth Paralobesia viteana ) containing impurities of isomeric structures were synthesized via copper-catalyzed cross-coupling of ( Z )-1-phenoxyhex-2-ene and ( Z )-1-phenoxypent-2-ene, respectively, with Grignard compounds in the key stage.