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Article Abstract
We report the catalytic generation of a vinyl Pd-oxyallyl that dimerizes regiospecifically to form highly functionalized nonbridged cyclooctanoids. Such compounds are otherwise synthetically challenging, but highly useful in synthesis. This vinyl Pd-oxyallyl species demonstrates both electrophilic and nucleophilic properties. DFT calculations elucidate the mechanism and the origins of the chemoselective cyclooctanoid formation.
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Ambiphilic Reactivity of Vinyl Pd-Oxyallyl for Expeditious Construction of Highly Functionalized Cyclooctanoids.
Org Lett
October 2021
Frontier Institute of Science and Technology (FIST), Xi'an Jiaotong University, Xi'an 710045, China.
We report the catalytic generation of a vinyl Pd-oxyallyl that dimerizes regiospecifically to form highly functionalized nonbridged cyclooctanoids. Such compounds are otherwise synthetically challenging, but highly useful in synthesis. This vinyl Pd-oxyallyl species demonstrates both electrophilic and nucleophilic properties.
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Department of Chemistry and Biochemistry , University of California, Los Angeles , California 90095-1569 , United States.
The (3+2) cycloadditions between electron-deficient Pd-oxyallyls and conjugated dienes have been investigated with density functional theory calculations. A stepwise mechanism with C-C bond formation occurring first is supported by computations. The key electron-withdrawing ester substituent on the Pd-oxyallyl species decreases the migratory insertion barrier by both lowering the LUMO energy and enabling a less-strained six-membered coordination mode.
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