Asymmetric Domino Heck Arylation and Alkylation of Nonconjugated Dienes: Double C–F···Sodium Attractive Noncovalent Interaction
- 1 September 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (18), 7064-7068
- https://doi.org/10.1021/acs.orglett.1c02457
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.Funding Information
- Peking University
- GlaxoSmithKline
- National Natural Science Foundation of China (NSFC 21933004)
- Nanyang Technological University
- Singapore Economic Development Board Trust Fund
- Shenzhen Bay Laboratory
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