(2E,4E)-, (2Z,4E)-, and (2E,4Z)-2,4-Alkadienoates can be synthesized in high yields by the cross-coupling of ethyl (E)-3-bromoacrylate, methyl (E)-3-bromo-2-methylpropenoate, ethyl (Z)-3-bromocrotonate,1-bromo-2-(ethoxycarbonyl)cyclohexene, and 4-bromocoumarin with 2-[(E)-1-alkenyl]-1,3,2-benzodioxaboroles or diisopropyl (Z)-1-hexenylboronate in the presence of 3 mol% of Pd(OAc)2, 6 mol% of PPh3, and 2 equivalents of Na2CO3 or K2CO3 in alcoholic solvents while retaining the original configuration of the double bonds in β-bromo esters and 1-alkenylboronates. Although the coupling reaction with 1-hexenylboronate with (Z)-3-bromoacrylate gave a mixture of ethyl (2Z,4E)- and (2E,4E)-nonadienoates in a ratio of 63 : 37, it was found that the use of bis(diphenylphosphino)ferrocene as a ligand of palladium brought about the stereoselective coupling under mild conditions.
(2E,4E)‐, (2Z,4E)‐ and (2E,4Z)‐2,4‐Alkadienoates can be synthesized in high yields by cross‐coupling of alkenes with alkenyl boron compounds in the presence of a Pd‐catalyst, Na2CO3 or K2CO3 and MeOH or EtOH.
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