Journal
ORGANIC LETTERS
Volume 25, Issue 38, Pages 6975-6981Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c02453
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In this study, highly regioselective hydrosilylation of cyclohexa-1,3-dienes bearing a tetrafluoroethylene group was achieved under mild conditions using 1-10 mol % Co-2(CO)(8) as the catalyst. Mechanistic studies and DFT calculations demonstrated that the reaction proceeds via the modified Chalk-Harrod mechanism, leading to the exclusive formation of homoallylsilanes. The successful synthesis of a tetrafluorinated negative-type liquid crystal showcased the synthetic utility of this hydrosilylation reaction.
Cyclohexa-1,3-dienes bearing a tetrafluoroethylene group underwent highly regioselective hydrosilylation in the presence of 1-10 mol % Co-2(CO)(8) in 1,2-dichloroethane under mild conditions (reflux, 3 h), which led to an abundant yield of homoallylsilanes. Mechanistic studies proved that the reaction proceeds as per the modified Chalk-Harrod mechanism; via DFT calculation, the reason for homoallylsilanes being exclusively obtained was demonstrated. The formal synthesis of a tetrafluorinated negative-type liquid crystal demonstrated the synthetic utility of such hydrosilylation.
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