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Asymmetric Domino Heck Arylation and Alkylation of Nonconjugated Dienes: Double C-F···Sodium Attractive Noncovalent Interaction.

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Palladium catalyzes a domino Heck arylation and alkylation of nonconjugated cyclodienes to produce trans isomers of disubstituted cyclohexenes in exceptionally high enantiomeric ratios, reaching 100:1 to 200:1 in many cases.… Click to show full abstract

Palladium catalyzes a domino Heck arylation and alkylation of nonconjugated cyclodienes to produce trans isomers of disubstituted cyclohexenes in exceptionally high enantiomeric ratios, reaching 100:1 to 200:1 in many cases. Importantly, the interactions of the two CF bonds of Josiphos and the sodium ion of malonates facilitates stereoselective allylic attack through DFT calculations and experiments. This is a new type of attractive noncovalent interactions found in organometallic catalysis.

Keywords: arylation alkylation; heck arylation; domino heck; attractive noncovalent; alkylation nonconjugated

Journal Title: Organic letters
Year Published: 2021

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