| abstract |
Provided is a method for efficiently producing an asymmetric conjugated diyne using an inexpensive and safe hydroxylamine hydrochloride substitute compound and a method for producing a Z, Z-conjugated diene compound from the obtained asymmetric conjugated diyne compound. A terminal alkyne compound (1) HC≡C-Z1-Y1 and an alkynyl halide (2) Y2-Z2-C≡C—X are hydrogenated in water and an organic solvent in the presence of a copper catalyst and a base. A method for producing an asymmetric conjugated diyne compound comprising at least a step of coupling with sodium borohydride to obtain an asymmetric conjugated diyne compound (3) Y2-Z2-C≡C—C≡C-Z1-Y1 is provided. Moreover, the manufacturing method of a Z, Z-conjugated diene compound by reduction etc. of the obtained asymmetric conjugated diyne compound is provided. [Selection figure] None |