Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups

A synthetic route to the bench-stable fluorinated masked carbene reagent diethyl 2-diazo-1,1,3,3,3-pentafluoropropylphosphonate, bearing a trifluoromethyl and a difluoromethyl group is reported for the first time. Its application in CuI-catalyzed cyclopropanation reactions with aromatic and aliphati...

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Autores principales: Hajdin, Ita, Pajkert, Romana, Keßler, Mira, Han, Jianlin, Mei, Haibo, Röschenthaler, Gerd-Volker
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10155617/
https://www.ncbi.nlm.nih.gov/pubmed/37153646
http://dx.doi.org/10.3762/bjoc.19.39
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author Hajdin, Ita
Pajkert, Romana
Keßler, Mira
Han, Jianlin
Mei, Haibo
Röschenthaler, Gerd-Volker
author_facet Hajdin, Ita
Pajkert, Romana
Keßler, Mira
Han, Jianlin
Mei, Haibo
Röschenthaler, Gerd-Volker
author_sort Hajdin, Ita
collection PubMed
description A synthetic route to the bench-stable fluorinated masked carbene reagent diethyl 2-diazo-1,1,3,3,3-pentafluoropropylphosphonate, bearing a trifluoromethyl and a difluoromethyl group is reported for the first time. Its application in CuI-catalyzed cyclopropanation reactions with aromatic and aliphatic terminal alkenes under mild reaction conditions is demonstrated. In total, sixteen new cyclopropanes were synthesized in good to very good yields.
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spelling pubmed-101556172023-05-04 Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups Hajdin, Ita Pajkert, Romana Keßler, Mira Han, Jianlin Mei, Haibo Röschenthaler, Gerd-Volker Beilstein J Org Chem Letter A synthetic route to the bench-stable fluorinated masked carbene reagent diethyl 2-diazo-1,1,3,3,3-pentafluoropropylphosphonate, bearing a trifluoromethyl and a difluoromethyl group is reported for the first time. Its application in CuI-catalyzed cyclopropanation reactions with aromatic and aliphatic terminal alkenes under mild reaction conditions is demonstrated. In total, sixteen new cyclopropanes were synthesized in good to very good yields. Beilstein-Institut 2023-04-25 /pmc/articles/PMC10155617/ /pubmed/37153646 http://dx.doi.org/10.3762/bjoc.19.39 Text en Copyright © 2023, Hajdin et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Letter
Hajdin, Ita
Pajkert, Romana
Keßler, Mira
Han, Jianlin
Mei, Haibo
Röschenthaler, Gerd-Volker
Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups
title Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups
title_full Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups
title_fullStr Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups
title_full_unstemmed Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups
title_short Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups
title_sort access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10155617/
https://www.ncbi.nlm.nih.gov/pubmed/37153646
http://dx.doi.org/10.3762/bjoc.19.39
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