Cargando…

Nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters

Herein, we report a nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes through reductive decarboxylation of redox-active esters. The present reaction enables the preparation of functionalized gem-difluoroalkenes with the formation of sterically hindered C(sp(3))–C(sp(3)) b...

Descripción completa

Detalles Bibliográficos
Autores principales: Lu, Xi, Wang, Xiao-Xu, Gong, Tian-Jun, Pi, Jing-Jing, He, Shi-Jiang, Fu, Yao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6345349/
https://www.ncbi.nlm.nih.gov/pubmed/30774875
http://dx.doi.org/10.1039/c8sc04335c
_version_ 1783389558201647104
author Lu, Xi
Wang, Xiao-Xu
Gong, Tian-Jun
Pi, Jing-Jing
He, Shi-Jiang
Fu, Yao
author_facet Lu, Xi
Wang, Xiao-Xu
Gong, Tian-Jun
Pi, Jing-Jing
He, Shi-Jiang
Fu, Yao
author_sort Lu, Xi
collection PubMed
description Herein, we report a nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes through reductive decarboxylation of redox-active esters. The present reaction enables the preparation of functionalized gem-difluoroalkenes with the formation of sterically hindered C(sp(3))–C(sp(3)) bonds under very mild reaction conditions, while tolerating many sensitive functional groups and requiring minimal substrate protection. Therefore, this method provides an efficient and convenient approach for late-stage modification of biologically interesting molecules.
format Online
Article
Text
id pubmed-6345349
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-63453492019-02-15 Nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters Lu, Xi Wang, Xiao-Xu Gong, Tian-Jun Pi, Jing-Jing He, Shi-Jiang Fu, Yao Chem Sci Chemistry Herein, we report a nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes through reductive decarboxylation of redox-active esters. The present reaction enables the preparation of functionalized gem-difluoroalkenes with the formation of sterically hindered C(sp(3))–C(sp(3)) bonds under very mild reaction conditions, while tolerating many sensitive functional groups and requiring minimal substrate protection. Therefore, this method provides an efficient and convenient approach for late-stage modification of biologically interesting molecules. Royal Society of Chemistry 2018-11-07 /pmc/articles/PMC6345349/ /pubmed/30774875 http://dx.doi.org/10.1039/c8sc04335c Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Lu, Xi
Wang, Xiao-Xu
Gong, Tian-Jun
Pi, Jing-Jing
He, Shi-Jiang
Fu, Yao
Nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters
title Nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters
title_full Nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters
title_fullStr Nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters
title_full_unstemmed Nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters
title_short Nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters
title_sort nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6345349/
https://www.ncbi.nlm.nih.gov/pubmed/30774875
http://dx.doi.org/10.1039/c8sc04335c
work_keys_str_mv AT luxi nickelcatalyzedallylicdefluorinativealkylationoftrifluoromethylalkeneswithreductivedecarboxylationofredoxactiveesters
AT wangxiaoxu nickelcatalyzedallylicdefluorinativealkylationoftrifluoromethylalkeneswithreductivedecarboxylationofredoxactiveesters
AT gongtianjun nickelcatalyzedallylicdefluorinativealkylationoftrifluoromethylalkeneswithreductivedecarboxylationofredoxactiveesters
AT pijingjing nickelcatalyzedallylicdefluorinativealkylationoftrifluoromethylalkeneswithreductivedecarboxylationofredoxactiveesters
AT heshijiang nickelcatalyzedallylicdefluorinativealkylationoftrifluoromethylalkeneswithreductivedecarboxylationofredoxactiveesters
AT fuyao nickelcatalyzedallylicdefluorinativealkylationoftrifluoromethylalkeneswithreductivedecarboxylationofredoxactiveesters