tBuOLi-Promoted Hydroboration of Esters and Epoxides

Commercially available and inexpensive lithium tert -butoxide ( t BuOLi) acts as a good precatalyst for the hydroboration of esters, lactones, and epoxides using pinacolborane as a borylation agent. Functional groups such as cyano-, nitro-, amino-, vinyl, and alkynyl are unaffected under the present...

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Published inACS omega Vol. 7; no. 22; pp. 18876 - 18886
Main Authors Shi, Yinyin, Wang, Yue, Huang, Zhefan, Zhang, Fangjun, Shao, Yinlin
Format Journal Article
LanguageEnglish
Published American Chemical Society 25.05.2022
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Summary:Commercially available and inexpensive lithium tert -butoxide ( t BuOLi) acts as a good precatalyst for the hydroboration of esters, lactones, and epoxides using pinacolborane as a borylation agent. Functional groups such as cyano-, nitro-, amino-, vinyl, and alkynyl are unaffected under the presented hydroboration process, representing high chemoselectivity. This transformation has also been effectively applied to the synthesis of key intermediates of Erlotinib and Cinacalcet. Preliminary investigations of the mechanism show that the hydroboration proceeds through the in situ formed BH 3 species.
ISSN:2470-1343
DOI:10.1021/acsomega.2c01866