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• W2010489169 abstract "Density functional theory (DFT) calculations with B3LYP and M06 functionals elucidated the reactivities of alkynes and Z/E selectivity of cyclodecatriene products in the Ni-catalyzed [4 + 4 + 2] cycloadditions of dienes and alkynes. The Ni-mediated oxidative cyclization of butadienes determines the Z/E selectivity. Only the oxidative cyclization of one s-cis to one s-trans butadiene is facile and exergonic, leading to the observed 1Z,4Z,8E-cyclodecatriene product. The same step with two s-cis or s-trans butadienes is either kinetically or thermodynamically unfavorable, and the 1Z,4E,8E- and 1Z,4Z,8Z-cyclodecatriene isomers are not observed in experiments. In addition, the competition between the desired cooligomerization and [2 + 2 + 2] cycloadditions of alkynes depends on the coordination of alkynes. With either electron-deficient alkynes or alkynes with free hydroxyl groups, the coordination of alkynes is stronger than that of dienes, and alkyne trimerization prevails. With alkyl-substituted alkynes, the generation of alkyne-coordinated nickel complex is much less favorable, and the [4 + 4 + 2] cycloaddition occurs." @default.
• W2010489169 created "2016-06-24" @default.
• W2010489169 creator A5003740475 @default.
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• W2010489169 date "2014-11-07" @default.
• W2010489169 modified "2023-09-25" @default.
• W2010489169 title "Mechanism, Reactivity, and Selectivity of Nickel-Catalyzed [4 + 4 + 2] Cycloadditions of Dienes and Alkynes" @default.
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• W2010489169 doi "https://doi.org/10.1021/jo502219d" @default.
• W2010489169 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/4275152" @default.
• W2010489169 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25325891" @default.
• W2010489169 hasPublicationYear "2014" @default.
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