4.8 Article

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

Journal

ORGANIC LETTERS
Volume 23, Issue 18, Pages 7064-7068

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02457

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Funding

  1. Peking University Shenzhen Graduate School
  2. National Natural Science Foundation of China (NSFC) [21933004]
  3. Nanyang Technological University
  4. GlaxoSmithKline
  5. Singapore Economic Development Board Trust Fund
  6. Shenzhen Bay Laboratory

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This study revealed that palladium catalyzes a domino Heck arylation and alkylation of nonconjugated cyclodienes to produce trans isomers of disubstituted cyclohexenes with exceptionally high enantiomeric ratios. Through DFT calculations and experiments, it was demonstrated that the interaction between the two CF bonds of Josiphos and the sodium ion of malonates facilitates stereoselective allylic attack. This represents a new type of attractive noncovalent interactions discovered in organometallic catalysis.
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.

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