The invention relates to a method for synthesizing a compound with a rotation-resistant 1, 3-
diene structure through a
transition metal catalytic reduction
coupling reaction, and discloses a method for synthesizing a compound with a rotation-resistant 1, 3-
diene structure by taking 1-bromo-3, 4-dihydronaphthalene-2-
formic acid phenyl ester and a derivative thereof as a substrate,
ethylene glycol
dimethyl ether nickel bromide (II) as a catalyst, activated
zinc powder as a
reducing agent,
cobalt phthalocyanine (II) as a
single electron transfer agent, (3aS, 3aS, 3aS, 3aS, 3aS, 3aS, 3aS, 3aS, 3aS, 3aS, 3aS, 3aS, 3aS, 3aS According to the method, 2, 2 '-[(phenyloxy) carbonyl]-1-(3, 4-dihydro)-dinaphthalene with a non-planar 1, 3-
diene structure and enantioselectivity and the derivative thereof are obtained through reaction at the temperature of 30 DEG C by taking 2, 2'-[(phenyloxy) carbonyl]-1-(3, 4-dihydro)-dinaphthalene as a
raw material, taking (3aR, 8aR)-2-(6-benzhydrylpyridine-2-yl)-8, 8a-dihydrotetrahydro-3aH-indeno [1, 2-d]
oxazole as a
chiral ligand, taking
tetraethylammonium iodide as an additive and taking
anhydrous toluene as a
solvent. The method has the advantages of high efficiency, simplicity, wide substrate application range, convenience in operation and the like, and an efficient and novel preparation method is provided for the rotation-resistant 1, 3-diene compound.