Defluorosilylation of fluoroarenes and fluoroalkanes

Benqiang Cui, Shichong Jia, Etsuko Tokunaga and Norio Shibata ()
Additional contact information
Benqiang Cui: Nagoya Institute of Technology, Gokiso
Shichong Jia: Nagoya Institute of Technology, Gokiso
Etsuko Tokunaga: Nagoya Institute of Technology, Gokiso
Norio Shibata: Nagoya Institute of Technology, Gokiso

Nature Communications, 2018, vol. 9, issue 1, 1-8

Abstract: Abstract Direct activation of carbon–fluorine bonds (C–F) to introduce the silyl or boryl groups and generate valuable carbon–silicon (C–Si) or carbon–boron (C–B) bonds is important in the development of synthetically useful reactions, owing to the unique opportunities for further derivatization to achieve more complex molecules. Despite considerable progress of C–F bond activation to construct carbon–carbon (C–C) and carbon–heteroatom (C–X) bond formation, the defluorosilylation via C–F cleavage has been rarely demonstrated. Here, we report an ipso-silylation of aryl fluorides via cleavage of unactivated C–F bonds by a Ni catalyst under mild conditions and without the addition of any external ligand. Alkyl fluorides are also directly converted into the corresponding alkyl silanes under similar conditions, even in the absence of the Ni catalyst. Applications of this protocol in late-stage defluorosilylation of potentially bioactive pharmaceuticals and in further derivatizations are also carried out.

Date: 2018
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-018-06830-w Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-06830-w

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-018-06830-w

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().