(t)BuOLi-Promoted Hydroboration of Esters and Epoxides

[Image: see text] 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...

Descripción completa

Detalles Bibliográficos
Autores principales: Shi, Yinyin, Wang, Yue, Huang, Zhefan, Zhang, Fangjun, Shao, Yinlin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9178618/
https://www.ncbi.nlm.nih.gov/pubmed/35694491
http://dx.doi.org/10.1021/acsomega.2c01866
_version_ 1784723099743158272
author Shi, Yinyin
Wang, Yue
Huang, Zhefan
Zhang, Fangjun
Shao, Yinlin
author_facet Shi, Yinyin
Wang, Yue
Huang, Zhefan
Zhang, Fangjun
Shao, Yinlin
author_sort Shi, Yinyin
collection PubMed
description [Image: see text] 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.
format Online
Article
Text
id pubmed-9178618
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-91786182022-06-10 (t)BuOLi-Promoted Hydroboration of Esters and Epoxides Shi, Yinyin Wang, Yue Huang, Zhefan Zhang, Fangjun Shao, Yinlin ACS Omega [Image: see text] 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. American Chemical Society 2022-05-25 /pmc/articles/PMC9178618/ /pubmed/35694491 http://dx.doi.org/10.1021/acsomega.2c01866 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Shi, Yinyin
Wang, Yue
Huang, Zhefan
Zhang, Fangjun
Shao, Yinlin
(t)BuOLi-Promoted Hydroboration of Esters and Epoxides
title (t)BuOLi-Promoted Hydroboration of Esters and Epoxides
title_full (t)BuOLi-Promoted Hydroboration of Esters and Epoxides
title_fullStr (t)BuOLi-Promoted Hydroboration of Esters and Epoxides
title_full_unstemmed (t)BuOLi-Promoted Hydroboration of Esters and Epoxides
title_short (t)BuOLi-Promoted Hydroboration of Esters and Epoxides
title_sort (t)buoli-promoted hydroboration of esters and epoxides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9178618/
https://www.ncbi.nlm.nih.gov/pubmed/35694491
http://dx.doi.org/10.1021/acsomega.2c01866
work_keys_str_mv AT shiyinyin tbuolipromotedhydroborationofestersandepoxides
AT wangyue tbuolipromotedhydroborationofestersandepoxides
AT huangzhefan tbuolipromotedhydroborationofestersandepoxides
AT zhangfangjun tbuolipromotedhydroborationofestersandepoxides
AT shaoyinlin tbuolipromotedhydroborationofestersandepoxides

Ejemplares similares