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Synthesis of 1,3-dienes

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A wide range of aryl and vinylic halides react with 1,1-dimethylallene and potassium carbonate in the presence of Pd(dba)2 in N,N-dimethylacetamide to provide dienes in very good yields. Tetramethylallene, 1-methyl-1-phenylallene, 1-methyl-3-phenylallene, and 1-cyclohexylallene also react with aryl and vinylic halides to give diene products.
H.-M. Chang, C.-H. Cheng, J. Org. Chem., 2000, 65, 1767-1773.


An indium-mediated coupling of 1,4-dibromo-2-butyne with carbonyl compounds in aqueous media provides 1,3-butadien-2-ylmethanols in good yields.
W. Lu, J. Ma, Y. Yang, T. H. Chan, Org. Lett., 2000, 2, 3469-3471.


An efficient method for the preparation of various 2-aminomethyl-1,3-dienes was developed through the reaction of imines with an organoindium reagent generated in situ from indium and 1,3-dibromo-2-butyne. Three-component reactions of aldehydes, amines, and organoindium reagents gave successful results in a one-pot process.
D. Seomoon, J. A, P. H. Lee, Org. Lett., 2009, 11, 2401-2404.


A nickel-catalyzed reaction of 1,3-dicarbonyl compounds with α-methyl-substituted propargylic carbonate incorporates a 1,3-dienyl unit at the α-position of the 1,3-dicarbonyl compound.
N. Ishida, Y. Kamino, M. Murakami, Synlett, 2021, 32, 1621-1624.