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

Abstract

(8Z)-Dodec-8-en-1-yl acetate (pheromone of oriental fruit moth Grapholita molesta) and (9Z)-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.