Boric acid as a precatalyst for BH-catalyzed hydroboration

We report that boric acid, BO 3 H 3 , is a good precatalyst for the BH 3 -catalyzed hydroboration of esters using pinacolborane as a borylation agent. Using microwave irradiation as an energy source, we demonstrated that a dozen esters were converted into the corresponding boronate ethers in good yi...

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Veröffentlicht in:RSC advances 2021-09, Vol.11 (51), p.31941-31949
Hauptverfasser: Légaré Lavergne, Julien, To, Hoang-Minh, Fontaine, Frédéric-Georges
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Zusammenfassung:We report that boric acid, BO 3 H 3 , is a good precatalyst for the BH 3 -catalyzed hydroboration of esters using pinacolborane as a borylation agent. Using microwave irradiation as an energy source, we demonstrated that a dozen esters were converted into the corresponding boronate ethers in good yields. It was also possible to use boric acid as a precatalyst to reduce carbonates and alkynes. Considering the hazardous and pyrophoric nature of BH 3 solutions, boric acid proves to be a safe and green precatalyst for the metal-free reduction of unsaturated species. Cheap and air-stable boric acid is shown to be a good precatalyst for BH 3 hydroboration of esters and carbonates.
ISSN:2046-2069
DOI:10.1039/d1ra05945a